Water → 4-Bromo-2-methyl-N-(2,2,2-trifluoro-ethyl)-benzamide

HRID 910360Notes

Reaction equation

HRID 910360 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([CH3:11])[CH:3]=1.[F:12][C:13]([F:17])([F:16])[CH2:14][NH2:15].Cl.C(N(CC)CCCN=C=NCC)C.O>CN(C)C=O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:15][CH2:14][C:13]([F:17])([F:16])[F:12])=[O:8])=[C:4]([CH3:11])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 995704-Bromo-2-methylbenzoic acidHCID 99645121-(3-Diethylaminopropyl)-3-ethylcarbodiimide hydrochloride

Product 1

HCID 667843104-Bromo-2-methyl-N-(2,2,2-trifluoro-ethyl)-benzamideYield 58.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a solution of 5.00 g of 4-bromo-2-methyl benzoic acid and 3.45 g of 2,2,2-trifluoroethylamine in 30 ml of N,N-dimethylformamide, 5.79 g of 1-[3-(diethylamino)propyl]-3-ethylcarbodiimide hydrochloride was added with stirring at room temperature, and stirred at the same temperature for 1.5 hour. After the completion of the reaction, 80 ml of water was added, and precipitated crystal was filtered off, washed with water and dried to obtain 4.00 g of the aimed product as white crystal.

Workup

  1. stirringstirred at the same temperature for 1.5 hour
  2. additionwas added
  3. customprecipitated crystal
  4. filtrationwas filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-06ce5f2872c44d4487047e8126c8a898
Source dataset
uspto-grants-2011_09
Patent number
US08022089B2

Reaction notes

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