Triethylamine → 2,6-difluoro-N-formyl-N-vinyl-benzamide

HRID 1479156

반응식

HRID 1479156 반응식
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](Cl)=[O:5].[CH:12]([NH:14][CH:15]=[O:16])=[CH2:13].C(N(CC)CC)C.C(OC)(C)(C)C>CN(C)C1C=CN=CC=1.ClCCl.O>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([N:14]([CH:15]=[O:16])[CH:12]=[CH2:13])=[O:5]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 83191N-VinylformamideHCID 874382,6-Difluorobenzoyl chloride

생성물 1

HCID 897607692,6-difluoro-N-formyl-N-vinyl-benzamide수율 87%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

2,6-difluorobenzoyl chloride (35.4 ml, 50 g, 284 mmol) was added dropwise with stirring to a solution of N-vinylformamide (18 ml, 18.3 g, 258 mmol), 4-dimethylaminopyridine (3.1 g, 25.8 mmol), and triethylamine (53.8 ml, 39 g, 387 mmol) in dichloromethane (200 ml). The temperature was kept at ca 20° C. with an ice/water bath. After the addition the mixture was stirred two hours at room temperature then shaken between tBuOMe and water. The organic phase was washed with half saturated brine, dried with Na2SO4 and evaporated to give 47 g (87% crude) of 2,6-difluoro-N-formyl-N-vinyl-benzamide, which contained ca 60% of 2,6-difluoro-N-vinyl-benzamide, which is the product of the next step, in which the formyl group has already been cleaved.

후처리

  1. customThe temperature was kept at ca 20° C. with an ice/water bath
  2. additionAfter the addition the mixture
  3. washThe organic phase was washed with half saturated brine
  4. dry with materialdried with Na2SO4
  5. customevaporated

출처 및 근거

ORD 기록
ord-3c297fe837944e6ba6e9cec933846fa3
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09408392B2

연결된 노트

불러오는 중…