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

HRID 452488
Notes
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Reaction equation

HRID 452488 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228
Dimethylformamide
Solvent

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-ce9d8834890c497b84e596722dc2eec6
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492311B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes