Propylamine → 2,6-difluoro-N-vinyl-benzamide

HRID 1479157

Reaction equation

HRID 1479157 reaction equation
C(N)CC.[F:5][C:6]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:7]=1[C:8]([N:10](C=O)[CH:11]=[CH2:12])=[O:9]>ClCCl>[F:5][C:6]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:7]=1[C:8]([NH:10][CH:11]=[CH2:12])=[O:9]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 897607692,6-difluoro-N-formyl-N-vinyl-benzamide

Product 1

HCID 897607822,6-difluoro-N-vinyl-benzamideYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

n-Propylamine (36.7 ml, 26.33 g, 444 mmol) was added to a solution of crude 2,6-difluoro-N-formyl-N-vinyl-benzamide from step a (47 g, 222 mmol) in dichloromethane (200 ml). There was a weak exotherm. The reaction mixture was kept at room temperature with a cold water bath. The solution was then concentrated on the rotovap to give a brown oil, which was crystallised from ethanol/water to yield 30 g (75%) of pure 2,6-difluoro-N-vinyl-benzamide as beige crystals. A further 5.7 g was crystallised from concentration of the mother liquors. M.p. 103-107° C.

Workup

  1. customThe reaction mixture was kept at room temperature with a cold water bath
  2. concentrationThe solution was then concentrated on the rotovap
  3. customto give a brown oil, which
  4. customwas crystallised from ethanol/water

Sources & evidence

ORD record
ord-0ebfbf5bc9024a329865b68ac8740637
Source dataset
uspto-grants-2016_08
Patent number
US09408392B2

Linked notes

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