4-Methyl-3-nitroaniline → Benzamide

Thionyl chloride (576.0 g, 4.8 mol) was added over a period of 15 min to a solution of 3,5-bis trifluoro methyl benzoic acid (Lancaster) (250.0 g, 0.97 mol) in chloroform (2.5 L) at room temperature. The reaction mixture was heated to reflux temperature for 1 hour. The excess of thionyl chloride was removed by co-distillation with chloroform under reduced pressure. After the end of the distillation, the resulting 3,5-bis trifluoro methyl benzoyl chloride was cooled down to room temperature and dissolved in 400 ml chloroform. A solution of 4-methyl-3-nitroaniline (92.0 g, 0.60 mol) in chloroform (1.2 L) was cooled to −5° C. and triethyl amine (304.8 g, 3.0 mol) was added. 3,5-bis trifluoro methyl benzoyl chloride in chloroform was added drop wise at −5° C. over a period of 60-75 min. The resulting suspension was stirred for 1 hr at −5° C. The suspension was distilled to a residual volume of 800 ml and filtered, washed with chilled chloroform (200 ml) and dried in vacuum to give 160.0 g of novel (3,5-bis trifluoromethyl)-N-(4-methyl-3-nitrophenyl)-)-benzamide (68%) as cream colored crystals (98.2% purity by HPLC) MR-123-130° C.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux temperature for 1 hour
3. customThe excess of thionyl chloride was removed by co-distillation with chloroform under reduced pressure
4. distillationAfter the end of the distillation
5. dissolutiondissolved in 400 ml chloroform
6. distillationThe suspension was distilled to a residual volume of 800 ml
7. filtrationfiltered
8. washwashed with chilled chloroform (200 ml)
9. customdried in vacuum

ORD record

ord-2189cc7e2c61434e8824ad46489de823

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08183253B2