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

HRID 1479156

反応式

HRID 1479156 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

HCID 897607692,6-difluoro-N-formyl-N-vinyl-benzamide収率 87%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3c297fe837944e6ba6e9cec933846fa3
出典データセット
uspto-grants-2016_08
特許番号
US09408392B2

関連ノート

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