Water → HCID 23298019, compound

HRID 1953787Notes

Reaction equation

HRID 1953787 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.[OH2:20].[C:21]([O:24][CH2:25][CH3:26])(=[O:23])[CH3:22]>>[CH3:1][C:2]1[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=[CH:5][C:3]=1[NH:4][C:22](=[O:20])[C:21]([O:24][CH2:25][CH3:26])=[O:23]

Participants

5

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 137504374-Amino-3-methylbenzotrifluoride

Product 1

HCID 23298019HCID 23298019, compound

Procedure

A solution of 37.5 g (214 mmol) of 2-methyl-4-trifluoromethylaniline (DE 2750170 A1) and 44.7 ml (321 mmol) of triethylamine in 750 ml of ethyl acetate is cooled to +3° C. by means of an icebath. Ethyl oxalyl chloride (26.2 ml, 235.5 mmol) is slowly added dropwise so that the temperature does not rise above +10° C. The mixture is then stirred for a further 2 hours. The mixture is treated with water, washed with a 10% aqueous sodium hydrogencarbonate solution and with brine, dried over sodium sulfate and concentrated. Crystallization of the crude product affords 52.75 g of the title compound as white crystals.

Workup

  1. customdoes not rise above +10° C
  2. washwashed with a 10% aqueous sodium hydrogencarbonate solution and with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customCrystallization of the crude product

Sources & evidence

ORD record
ord-df7eed9334ae4e33bb53d0045a419f17
Source dataset
uspto-grants-2000_09
Patent number
US06117873

Reaction notes

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