1-(3,4-dichlorophenyl)-3-methylthiourea

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 1,2-dichloro-4-isothiocyanatobenzene (1 g, 4.9 mmol) in ethanol (30 mL) was added 8M methyl amine in ethanol (0.613 mL, 4.9 mmol) and the reaction was heated at 80° C. overnight. The solvent was removed under vacuum and the residue was washed with diethyl ether (10 mL) and dried to give crude 1-(3,4-dichlorophenyl)-3-methylthiourea as an off white solid (0.8 g, 69%). 1HNMR: 400 MHz, DMSO-d6: δ 2.93 (d, J=4.40 Hz, 3H), 7.37 (d, J=7.60 Hz, 1H), 7.55 (d, J=8.40 Hz, 1H), 7.86 (d, J=2.40 Hz, 1H), 7.92 (bs, 1H), 9.74 (bs, 1H). The solvent was removed under vacuum the residue was washed with diethyl ether (10 mL) dried

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

Procedure: Prepared by the method described in Example 1 from N-methyl-N'-(3,4-dichlorophenyl)thiourea (4.9 g, 21 mmoles) and acetylenedicarboxylic acid (2.6 g, 22 mmoles). Recrystallization from ethyl acetate gave the product (4.5 g), mp 225°-226° C. Prepared by the method Recrystallization from ethyl acetate

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

Procedure: Prepared by the method described in Example 1 from N-methyl-N'-(3,4-dichlorophenyl)thiourea (4.9 g, 21 mmoles) and acetylenedicarboxylic acid (2.6 g, 22 mmoles). Recrystallization from ethyl acetate gave the product (4.5 g), mp 225°-226° C. Prepared by the method Recrystallization from ethyl acetate

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 1,2-dichloro-4-isothiocyanatobenzene (1 g, 4.9 mmol) in ethanol (30 mL) was added 8M methyl amine in ethanol (0.613 mL, 4.9 mmol) and the reaction was heated at 80° C. overnight. The solvent was removed under vacuum and the residue was washed with diethyl ether (10 mL) and dried to give crude 1-(3,4-dichlorophenyl)-3-methylthiourea as an off white solid (0.8 g, 69%). 1HNMR: 400 MHz, DMSO-d6: δ 2.93 (d, J=4.40 Hz, 3H), 7.37 (d, J=7.60 Hz, 1H), 7.55 (d, J=8.40 Hz, 1H), 7.86 (d, J=2.40 Hz, 1H), 7.92 (bs, 1H), 9.74 (bs, 1H). The solvent was removed under vacuum the residue was washed with diethyl ether (10 mL) dried

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

Procedure: Prepared by the method described in Example 1 from N-methyl-N'-(3,4-dichlorophenyl)thiourea (4.9 g, 21 mmoles) and acetylenedicarboxylic acid (2.6 g, 22 mmoles). Recrystallization from ethyl acetate gave the product (4.5 g), mp 225°-226° C. Prepared by the method Recrystallization from ethyl acetate