2-chloro-N-methoxyacetamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compound was prepared by the method of Preparation 4 from methyl chloroacetohydroxamate and E-2-hydroxyimino-2-(thien-2-yl)acetic acid, νmax (Nujol) 3380 (--NH--), 1750, 1729 (--CO2H), 3700-2400 (bonded OH), 1690 cm-1 (--CONH--), τ(DMSO d6) 2.2-3.0 (thienyl), 5.49 (--OCH2CO--), 6.38 (--OCH3). Yield 34%.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compound was prepared by the method of Preparation 4 from methyl chloroacetohydroxamate and E-2-hydroxyimino-2-(thien-2-yl)acetic acid, νmax (Nujol) 3380 (--NH--), 1750, 1729 (--CO2H), 3700-2400 (bonded OH), 1690 cm-1 (--CONH--), τ(DMSO d6) 2.2-3.0 (thienyl), 5.49 (--OCH2CO--), 6.38 (--OCH3). Yield 34%.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium tert-butoxide (6.73 g) was stirred in dry dimethylsulphoxide (30 ml), then Z-2-(fur-2-yl)-2-hydroxyiminoacetic acid (3.11 g) was added to the suspension, which was cooled in an ice-bath, and the mixture was stirred for 1 hr. Methyl chloroacetohydroxamate (2.35 g) in dimethylsulphoxide (2 ml) was added dropwise. The mixture was stirred for 2 hr at room temperature and the resulting solution was poured into ice and water (125 ml). The pH was adjusted to 1 and the solution was saturated with sodium chloride and extracted with ethyl acetate (50+150+4×200 ml), the pH being kept at 1 by addition of more hydrochloric acid as necessary. The ethyl acetate solution was washed with saturated brine (2×50 ml), then dried (Na2SO4) and evaporated, leaving a pale-brown solid. Washing the solid with dichloromethane left the title-compound, 1.56 g, m.p. 129° (decomp.) λmax (EtOH) 272.5 nm (ε 14,700), νmax (Nujol) 3180 (bonded NH), 1753 (CO2H), 1612 and 1522 cm-1 (bonded CONH), τ(DMSO d6) 2.10, 3.15, 3.30 (α-furyl), ca. 4.45 (NH, CO2H), 5.42 (CH2), 6.35 (OCH3). was cooled in an ice-bath The mixture was stirred for 2 hr at room temperature extracted with ethyl acetate (50+150+4×200 ml) the pH being kept at 1 by addition of more hydrochloric acid as necessary The ethyl acetate solution was washed with saturated brine (2×50 ml) dried (Na2SO4) evaporated leaving a pale-brown solid Washing the solid with dichloromethane left the title-compound, 1.56 g, m.p. 129° (decomp.) λmax (EtOH) 272.5 nm (ε 14,700), νmax (Nujol) 3180 (bonded NH), 1753 (CO2H), 1612 and 1522 cm-1 (bonded CONH), τ(DMSO d6) 2.10, 3.15, 3.30 (α-furyl), ca. 4.45 (NH, CO2H), 5.42 (CH2), 6.35 (OCH3)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium tert-butoxide (6.73 g) was stirred in dry dimethylsulphoxide (30 ml), then Z-2-(fur-2-yl)-2-hydroxyiminoacetic acid (3.11 g) was added to the suspension, which was cooled in an ice-bath, and the mixture was stirred for 1 hr. Methyl chloroacetohydroxamate (2.35 g) in dimethylsulphoxide (2 ml) was added dropwise. The mixture was stirred for 2 hr at room temperature and the resulting solution was poured into ice and water (125 ml). The pH was adjusted to 1 and the solution was saturated with sodium chloride and extracted with ethyl acetate (50+150+4×200 ml), the pH being kept at 1 by addition of more hydrochloric acid as necessary. The ethyl acetate solution was washed with saturated brine (2×50 ml), then dried (Na2SO4) and evaporated, leaving a pale-brown solid. Washing the solid with dichloromethane left the title-compound, 1.56 g, m.p. 129° (decomp.) λmax (EtOH) 272.5 nm (ε 14,700), νmax (Nujol) 3180 (bonded NH), 1753 (CO2H), 1612 and 1522 cm-1 (bonded CONH), τ(DMSO d6) 2.10, 3.15, 3.30 (α-furyl), ca. 4.45 (NH, CO2H), 5.42 (CH2), 6.35 (OCH3). was cooled in an ice-bath The mixture was stirred for 2 hr at room temperature extracted with ethyl acetate (50+150+4×200 ml) the pH being kept at 1 by addition of more hydrochloric acid as necessary The ethyl acetate solution was washed with saturated brine (2×50 ml) dried (Na2SO4) evaporated leaving a pale-brown solid Washing the solid with dichloromethane left the title-compound, 1.56 g, m.p. 129° (decomp.) λmax (EtOH) 272.5 nm (ε 14,700), νmax (Nujol) 3180 (bonded NH), 1753 (CO2H), 1612 and 1522 cm-1 (bonded CONH), τ(DMSO d6) 2.10, 3.15, 3.30 (α-furyl), ca. 4.45 (NH, CO2H), 5.42 (CH2), 6.35 (OCH3)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Methoxychloroacetamide (12.3 grams; 0.1 mole), benzene (75 ml) and triethylamine (12 grams; 1.2 mole) are charged into a glass reaction flask equipped with a mechanical stirrer, therometer and reflux condenser. N,N-Dimethylcarbamoyl chloride (11 grams; 0.1 mole) dissolved in benzene (25 ml) is incrementally added to the reaction mixture, with stirring, at room temperature. After the addition is completed the reaction mixture is heated at reflux for a period of about 3 hours. After this time the reaction mixture is distilled to remove benzene and unreacted starting material thereby yielding the desired product 1-chloro-2-(N,N-dimethylcarbamoyloxy)-2-methoxyiminoethane. equipped with a mechanical stirrer therometer and reflux condenser is incrementally added to the reaction mixture After the addition is heated at reflux for a period of about 3 hours After this time the reaction mixture is distilled to remove benzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Methoxychloroacetamide (3.5 grams), benzene (60 ml) and dibutyltin dilaurate (1 drop) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. Methyl isocyanate (2.0 grams) dissolved in benzene (15 ml) was added dropwise to the reaction mixture at room temperature and with stirring. After the addition was completed the reaction mixture was heated at reflux, with stirring for a period of about 2 hours. After this time the reaction mixture was distilled to remove benzene and unreacted isocyanate leaving an oily residue. The residue was subjected to vacuum (0.1 mm Hg) whereupon it solidified. The solid was recrystallized from a carbon tetrachloride-hexane mixture to yield a white crystalline solid. The solid was washed with hexane and dried to yield the desired product 1-chloro-2-(N-methylcarbamoyloxy)-2-methoxyiminoethane having a melting point of 80°-82°C. equipped with a mechanical stirrer thermometer and reflux condenser was added dropwise to the reaction mixture at room temperature After the addition was heated at reflux with stirring for a period of about 2 hours After this time the reaction mixture was distilled to remove benzene and unreacted isocyanate leaving an oily residue The solid was recrystallized from a carbon tetrachloride-hexane mixture to yield a white crystalline solid The solid was washed with hexane dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Methoxychloroacetamide (12.3 grams; 0.1 mole), benzene (80 ml) and dibutyltin dilaurate (1 drop) are charged into a glass reaction flask equipped with a mechanical stirrer, thermometer and reflux condenser. 3-Allylphenylisocyanate (16 grams; 0.1 mole) dissolved in benzene (30 ml) is incrementally added to the reaction mixture, with stirring, at room temperature. After the addition is completed the reaction mixture is heated at reflux for a period of about 2 hours. After this time the reaction mixture is distilled to remove benzene and unreacted starting material thereby yielding the desired product 1-chloro-2-(N-3-allylphenylcarbamoyloxy)-2-methoxyiminoethane. equipped with a mechanical stirrer thermometer and reflux condenser is incrementally added to the reaction mixture After the addition is heated at reflux for a period of about 2 hours After this time the reaction mixture is distilled to remove benzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Methoxychloroacetamide (12.3 grams; 0.1 mole), benzene (80 ml) and dibutyltin dilaurate (1 drop) are charged into a glass reaction flask equipped with a mechanical stirrer, thermometer and reflux condenser. 4-Nitrophenylisocyanate (16.4 grams; 0.1 mole) dissolved in benzene (30 ml) is incrementally added to the reaction mixture, with stirring, at room temperature. After the addition is completed the reaction mixture is heated at reflux for a period of about 4 hours. After this time the reaction mixture is distilled to remove benzene and unreacted starting material thereby yielding the desired product 1-chloro-2-(N-4-nitrophenylcarbamoyloxy)-2-methoxyiminoethane. equipped with a mechanical stirrer thermometer and reflux condenser is incrementally added to the reaction mixture After the addition is heated at reflux for a period of about 4 hours After this time the reaction mixture is distilled to remove benzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Methoxychloroacetamide (12.3 grams; 0.1 mole), benzene (60 ml) and dibutyltin dilaurate (1 drop) are charged into a glass reaction flask equipped with a mechanical stirrer, thermometer and reflux condenser. 2-Methyl-4-methylthiophenylisocyanate (21.5 grams; 0.12 mole) dissolved in benzene (30 ml) is incrementally added to the reaction mixture, with stirring, at room temperature. After the addition is completed the reaction mixture is heated at reflux for a period of about 2 hours. After this time the reaction mixture is distilled to remove benzene and unreacted starting material thereby yielding the desired product 1-chloro-2-[N-(2-methyl-4-methylthiophenyl)carbamoyloxy]-2-methoxyiminoethane. equipped with a mechanical stirrer thermometer and reflux condenser is incrementally added to the reaction mixture After the addition is heated at reflux for a period of about 2 hours After this time the reaction mixture is distilled to remove benzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Methoxychloroacetamide (12.3 grams; 0.1 mole), benzene (60 ml) and dibutyltin dilaurate (1 drop) are charged into a glass reaction flask equipped with a mechanical stirrer, thermometer and reflux condenser. 2-Methoxyphenylisocyanate (15 grams; 0.1 mole) dissolved in benzene (30 ml) is incrementally added to the reaction mixture, with stirring, at room temperature. After the addition is completed the reaction mixture is heated at reflux for a period of about 3 hours. After this time the reaction mixture is distilled to remove benzene and unreacted starting material thereby yielding the desired product 1-chloro-2-[N-(2-methoxyphenyl)carbamoyloxy]-2-methoxyiminoethane. equipped with a mechanical stirrer thermometer and reflux condenser is incrementally added to the reaction mixture After the addition is heated at reflux for a period of about 3 hours After this time the reaction mixture is distilled to remove benzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compound was prepared by the method of Preparation 4 from methyl chloroacetohydroxamate and E-2-hydroxyimino-2-(thien-2-yl)acetic acid, νmax (Nujol) 3380 (--NH--), 1750, 1729 (--CO2H), 3700-2400 (bonded OH), 1690 cm-1 (--CONH--), τ(DMSO d6) 2.2-3.0 (thienyl), 5.49 (--OCH2CO--), 6.38 (--OCH3). Yield 34%.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium tert-butoxide (6.73 g) was stirred in dry dimethylsulphoxide (30 ml), then Z-2-(fur-2-yl)-2-hydroxyiminoacetic acid (3.11 g) was added to the suspension, which was cooled in an ice-bath, and the mixture was stirred for 1 hr. Methyl chloroacetohydroxamate (2.35 g) in dimethylsulphoxide (2 ml) was added dropwise. The mixture was stirred for 2 hr at room temperature and the resulting solution was poured into ice and water (125 ml). The pH was adjusted to 1 and the solution was saturated with sodium chloride and extracted with ethyl acetate (50+150+4×200 ml), the pH being kept at 1 by addition of more hydrochloric acid as necessary. The ethyl acetate solution was washed with saturated brine (2×50 ml), then dried (Na2SO4) and evaporated, leaving a pale-brown solid. Washing the solid with dichloromethane left the title-compound, 1.56 g, m.p. 129° (decomp.) λmax (EtOH) 272.5 nm (ε 14,700), νmax (Nujol) 3180 (bonded NH), 1753 (CO2H), 1612 and 1522 cm-1 (bonded CONH), τ(DMSO d6) 2.10, 3.15, 3.30 (α-furyl), ca. 4.45 (NH, CO2H), 5.42 (CH2), 6.35 (OCH3). was cooled in an ice-bath The mixture was stirred for 2 hr at room temperature extracted with ethyl acetate (50+150+4×200 ml) the pH being kept at 1 by addition of more hydrochloric acid as necessary The ethyl acetate solution was washed with saturated brine (2×50 ml) dried (Na2SO4) evaporated leaving a pale-brown solid Washing the solid with dichloromethane left the title-compound, 1.56 g, m.p. 129° (decomp.) λmax (EtOH) 272.5 nm (ε 14,700), νmax (Nujol) 3180 (bonded NH), 1753 (CO2H), 1612 and 1522 cm-1 (bonded CONH), τ(DMSO d6) 2.10, 3.15, 3.30 (α-furyl), ca. 4.45 (NH, CO2H), 5.42 (CH2), 6.35 (OCH3)