2-propan-2-yloxybenzoyl chloride

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 2-Isopropoxy-benzoyl chloride was condensed with 4-Amino-2-trifluoromethyl benzonitrile in dichloromethane in presence of triethylamine as acid scavenger to yield N-(4-Cyano-3-trifluoromethyl-phenyl)-2-Isopropoxy-benzamide. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product.

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

Procedure: 2-Isopropoxy-benzoyl chloride was condensed with 5-Amino-2-nitrobenzotrifluoride in dichloromethane in presence of triethylamine as acid scavenger to yield 2-Isopropoxy-N-(4-nitro-3-trifluoromethyl-phenyl)-benzamide. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product.

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

Procedure: 2-Isopropoxy-benzoyl chloride was condensed with 5-Amino-2-nitrobenzotrifluoride in dichloromethane in presence of triethylamine as acid scavenger to yield 2-Isopropoxy-N-(4-nitro-3-trifluoromethyl-phenyl)-benzamide. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product.

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

Procedure: 2-Isopropoxy-benzoyl chloride was condensed with 4-Amino-2-trifluromethyl benzonitrile in dichloromethane in presence of triethylamine as acid scavenger to yield N-4-Cyano-3-trifluoromethyl-phenyl)-2-Isopropoxy-benzamide. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product.

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

Procedure: 2-Isopropoxy-benzoyl chloride was condensed with 5-Amino-2-nitrobenzotrifluoride in dichloromethane in presence of triethylamine as acid scavenger to yield 2-Isopropoxy-N-(4-nitro-3-trifluromethyl-phenyl)-benzamide. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product.

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

Procedure: The procedure is the same as that described for isopropoxy benzoyl chloride. (2 g of the acid chloride was reacted at ambient temperature with 100 mg of SnCl4 for 2 hours and gave a red-brown solid with a dp of 4.4). gave a red-brown solid with a dp of 4.4)

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

Procedure: A sample vial was filled with 2 g of isopropoxy benzoyl chloride and SnCl4 was injected. The mixture was homogenized and then kept at the reaction temperature chosen. After the reaction 50 mg of the solidified red-brown reaction mixture was hydrolyzed in 1 ml of a mixture of CD3OD/D2O/NaOD (12:3:1, weight ratios) (2 hours, 60° C.) and the degree of polymerization (dp) was determined by NMR end-group analysis. the degree of polymerization (dp)

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

Procedure: Dimethyl-4-amino-isophthalate (10 g) in 10 ml of dioxane and 20 ml of anhydrous pyridine are treated with 20 g of 2-isopropoxy-benzoyl chloride at room temperature, overnight. After dilution with water, the precipitate is collected, dissolved in ethyl acetate, and washed with 5% NaHCO3 and then with water. After evaporation to dryness under vacuum, the material is crystallized from isopropyl ether, yielding dimethyl-4-(2'-isopropoxybenzoylamino)-isophthalate (12.3 g; m.p. 107°-110° C.), which is dissolved in 80 ml of dioxane and treated with 80 ml of 1 N NaOH at room temperature for one night. After acidification with dilute HCl, the precipitate is collected under vacuum and washed with water until neutral. The yield is 10.9 g of 4-(2'-isopropoxybenzoylamino)-isophthalic acid, which are treated with 60 ml of acetic anhydride at 90°-100° C. for 15'. After cooling, dilute with 60 ml of isopropyl ether and filter. The yield is 9 g of 6-carboxy-2-(2'-isopropoxyphenyl)-4H-3,1-benzoxazin-4-one (m.p. 246°-250° C.), which are reacted at room temperature first with 90 ml of 32% ammonium hydroxide and then with 45 ml of 2 N NaOH for 120'. After acidification with 4 N HCl, the precipitate is filtered off and crystallized from ethanol-chloroform to give 6-carboxy-2-(2'-isopropoxyphenyl)-3,4-dihydro-4-oxo-quinazoline (6.6 g; m.p. 316°-318° C.). After dilution with water, the precipitate is collected dissolved in ethyl acetate washed with 5% NaHCO3 After evaporation to dryness under vacuum the material is crystallized from isopropyl ether