2-[N-(2-acetyloxyethyl)anilino]ethyl acetate

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 450 ml of dry dimethyl formamide were slowly added dropwise with stirring and at a temperature of 0°-10° C. 100 ml of freshly distilled phosphoroxytrichloride. This mixture was stirred for 2 hours at 20° C. To this mixture there was subsequently added dropwise with proper stirring and over a period of 60 minutes the crude reaction product of the previous step, viz. N,N-di(2-acetyloxyethyl)aniline, the reaction mixture being kept at a temperature of 20° C. Next, the reaction mixture was heated to 60° C. for 60 minutes and then poured, with vigorous stirring, into a mixture of 1 kg of ice and a solution of 525 g of sodium acetate trihydrate in 1 l of water. The organic layer was separated and the water layer was extracted four times, each time with 300 ml of dichloromethane. The combined organic layers were washed three times, each time with 200 ml of water, dried on magnesium sulphate, and concentrated by evaporation. The residue (about 280 g of dark brown oil), which consisted almost entirely of 4-di(2-acetyloxyethyl)aminobenzaldehyde, was used in the next step without further purification. This mixture was stirred for 2 hours at 20° C To this mixture there was subsequently added dropwise with proper stirring and over a period of 60 minutes the crude reaction product of the previous step, viz being kept at a temperature of 20° C The organic layer was separated the water layer was extracted four times The combined organic layers were washed three times each time with 200 ml of water, dried on magnesium sulphate concentrated by evaporation was used in the next step without further purification

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 450 ml of dry dimethyl formamide were slowly added dropwise with stirring and at a temperature of 0°-10° C. 100 ml of freshly distilled phosphoroxytrichloride. This mixture was stirred for 2 hours at 20° C. To this mixture there was subsequently added dropwise with proper stirring and over a period of 60 minutes the crude reaction product of the previous step, viz. N,N-di(2-acetyloxyethyl)aniline, the reaction mixture being kept at a temperature of 20° C. Next, the reaction mixture was heated to 60° C. for 60 minutes and then poured, with vigorous stirring, into a mixture of 1 kg of ice and a solution of 525 g of sodium acetate trihydrate in 1 l of water. The organic layer was separated and the water layer was extracted four times, each time with 300 ml of dichloromethane. The combined organic layers were washed three times, each time with 200 ml of water, dried on magnesium sulphate, and concentrated by evaporation. The residue (about 280 g of dark brown oil), which consisted almost entirely of 4-di(2-acetyloxyethyl)aminobenzaldehyde, was used in the next step without further purification. This mixture was stirred for 2 hours at 20° C To this mixture there was subsequently added dropwise with proper stirring and over a period of 60 minutes the crude reaction product of the previous step, viz being kept at a temperature of 20° C The organic layer was separated the water layer was extracted four times The combined organic layers were washed three times each time with 200 ml of water, dried on magnesium sulphate concentrated by evaporation was used in the next step without further purification

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 450 ml of dry dimethyl formamide were slowly added dropwise with stirring and at a temperature of 0°-10° C. 100 ml of freshly distilled phosphoroxytrichloride. This mixture was stirred for 2 hours at 20° C. To this mixture there was subsequently added dropwise with proper stirring and over a period of 60 minutes the crude reaction product of the previous step, viz. N,N-di(2-acetyloxyethyl)aniline, the reaction mixture being kept at a temperature of 20° C. Next, the reaction mixture was heated to 60° C. for 60 minutes and then poured, with vigorous stirring, into a mixture of 1 kg of ice and a solution of 525 g of sodium acetate trihydrate in 1 l of water. The organic layer was separated and the water layer was extracted four times, each time with 300 ml of dichloromethane. The combined organic layers were washed three times, each time with 200 ml of water, dried on magnesium sulphate, and concentrated by evaporation. The residue (about 280 g of dark brown oil), which consisted almost entirely of 4-di(2-acetyloxyethyl)aminobenzaldehyde, was used in the next step without further purification. This mixture was stirred for 2 hours at 20° C To this mixture there was subsequently added dropwise with proper stirring and over a period of 60 minutes the crude reaction product of the previous step, viz being kept at a temperature of 20° C The organic layer was separated the water layer was extracted four times The combined organic layers were washed three times each time with 200 ml of water, dried on magnesium sulphate concentrated by evaporation was used in the next step without further purification

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

Procedure: N,N-Di-(2-acetoxyethyl)aniline (A6) (126 g, 0.476 mol) was reacted with phosphorous oxychloride (80.3 g, 0.524 mol) in DMF as for A2 in Example 3. The product was distilled at 155°-175° C. (0.15 mm) to yield 130 g (93%) of A7 as an orange oil. The product was distilled at 155°-175° C. (0.15 mm)

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

Procedure: N,N-Di-(2-acetoxyethyl)aniline (A6) (126 g, 0.476 mol) was reacted with phosphorous oxychloride (80.3 g, 0.524 mol) in DMF as for A2 in Example 3. The product was distilled at 155°-175° C. (0.15 mm) to yield 130 g (93%) of A7 as an orange oil. The product was distilled at 155°-175° C. (0.15 mm)

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

Procedure: N,N-Di-(2-acetoxyethyl)aniline (A6) (126 g, 0.476 mol) was reacted with phosphorous oxychloride (80.3 g, 0.524 mol) in DMF as for A2 in Example 3. The product was distilled at 155°-175° C. (0.15 mm) to yield 130 g (93%) of A7 as an orange oil. The product was distilled at 155°-175° C. (0.15 mm)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 450 ml of dry dimethyl formamide were slowly added dropwise with stirring and at a temperature of 0°-10° C. 100 ml of freshly distilled phosphoroxytrichloride. This mixture was stirred for 2 hours at 20° C. To this mixture there was subsequently added dropwise with proper stirring and over a period of 60 minutes the crude reaction product of the previous step, viz. N,N-di(2-acetyloxyethyl)aniline, the reaction mixture being kept at a temperature of 20° C. Next, the reaction mixture was heated to 60° C. for 60 minutes and then poured, with vigorous stirring, into a mixture of 1 kg of ice and a solution of 525 g of sodium acetate trihydrate in 1 l of water. The organic layer was separated and the water layer was extracted four times, each time with 300 ml of dichloromethane. The combined organic layers were washed three times, each time with 200 ml of water, dried on magnesium sulphate, and concentrated by evaporation. The residue (about 280 g of dark brown oil), which consisted almost entirely of 4-di(2-acetyloxyethyl)aminobenzaldehyde, was used in the next step without further purification. This mixture was stirred for 2 hours at 20° C To this mixture there was subsequently added dropwise with proper stirring and over a period of 60 minutes the crude reaction product of the previous step, viz being kept at a temperature of 20° C The organic layer was separated the water layer was extracted four times The combined organic layers were washed three times each time with 200 ml of water, dried on magnesium sulphate concentrated by evaporation was used in the next step without further purification