Methylamine → N-(2-Hydroxy-1-methylcarbamoylbut-3-enyl)-4-fluoro-2-trifluoromethylbenzamide

HRID 506487Notes

Reaction equation

HRID 506487 reaction equation
[OH:1][CH:2]([CH:23]=[CH2:24])[CH:3]([NH:9][C:10](=[O:22])[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[C:18]([F:21])([F:20])[F:19])[C:4](OCC)=[O:5].[CH3:25][NH2:26]>CO>[OH:1][CH:2]([CH:23]=[CH2:24])[CH:3]([NH:9][C:10](=[O:22])[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[C:18]([F:21])([F:20])[F:19])[C:4](=[O:5])[NH:26][CH3:25]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59432152Ethyl 3-hydroxy-2-(4-fluoro-2-trifluoromethylbenzoylamino)pent-4-enoate

Product 1

HCID 59432158N-(2-Hydroxy-1-methylcarbamoylbut-3-enyl)-4-fluoro-2-trifluoromethylbenzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.5 g (12.9 mmol) of ethyl 3-hydroxy-2-(4-fluoro-2-trifluoromethylbenzoylamino)pent-4-enoate were dissolved in methanol. With ice cooling methylamine gas was introduced for 2 h. The reaction solution was then concentrated and washed. This gave 3.1 g (80% of theory) of the title compound as a colorless solid (diastereomer ratio 2:1).

Workup

  1. additionwas introduced for 2 h
  2. concentrationThe reaction solution was then concentrated
  3. washwashed

Sources & evidence

ORD record
ord-abcfde996bf247928a4a2c41a38f641c
Source dataset
uspto-grants-2010_08
Patent number
US07786046B2

Reaction notes

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