2,6-Dichlorophenol → 2,6-Dichloro-N-phenylaniline

37.6 g of 2,4,6-trimethyl phenol and 11 g of sodium hydroxide were dissolved in 30 ml of water and mixed with 150 ml of toluene. The toluene recovered from heating was mixed with 139 ml of N,N-dimethylformamide to obtain a N,N-dimethylformamide solution. 40 g of 2,6-dichlorophenol was dissolved in 130 ml of toluene, followed by the addition of 9.8 g of sodium hydroxide in 20 ml of water, 41.5 g of N-phenyl chloroacetamide and 8.7 ml of N,N-dimethylformamide, and refluxed in a oil bath at 140°-150° C. for 15 h. The toluene was recovered from the reflux, and mixed with the above N,N-dimethylformamide solution and reacted for 3 h. Recovering N,N-dimethylformamide from the reacted mixture with distillation under reduced pressure (145°-150° C., 8 mm Hg) resulted in the formation of 53 g of N-phenyl 2,6-dichloroaniline and the product yield was 90.75%.

1. customThe toluene recovered
2. temperaturefrom heating
3. additionwas mixed with 139 ml of N,N-dimethylformamide
4. customto obtain a N,N-dimethylformamide solution
5. temperaturerefluxed in a oil bath at 140°-150° C. for 15 h
6. customThe toluene was recovered from the reflux
7. additionmixed with the above N,N-dimethylformamide solution
8. customreacted for 3 h
9. distillationRecovering N,N-dimethylformamide from the reacted mixture with distillation under reduced pressure (145°-150° C., 8 mm Hg)

ORD record

ord-e630796d26034cbd8143e61006221e14

Source dataset

uspto-grants-1995_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05475139