Triethylamine → 3-(2,5-difluoro-phenyl)-N-methoxy-N-methyl-acrylamide

HRID 857016ノート

反応式

HRID 857016 の反応式
[F:1][C:2]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:3]=1[CH:4]=[CH:5][C:6](O)=[O:7].CCN=C=NCCC[N:22]([CH3:24])C.Cl.C(N(CC)CC)C.N[O:34][CH3:35].Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:1][C:2]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([N:22]([O:34][CH3:35])[CH3:24])=[O:7]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 5179803-(2,5-Difluoro-phenyl)-acrylic acidHCID 521874O-Methylhydroxylamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 738515783-(2,5-difluoro-phenyl)-N-methoxy-N-methyl-acrylamide収率 97.3%

試薬・触媒・溶媒 2

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

実験手順

A mixture of 2,5-difluorocinnamic acid (18.4 g), EDAC.HCl (23 g), DMAP (12.2 g), triethylamine (28 mL), and NH2OMe.HCl (12 g) in CH2Cl2 (300 mL) was stirred at room temperature for 16 h. The reaction was quenched with water, and the organic layer was washed with brine, dried over MgSO4 and filtered. The filtrated was evaporated in vacuo, and the crude product was purified by silica gel flash chromatography eluting with 33% hexanes in ethyl acetate gave the title compound (22.1 g) as a solid.

後処理

  1. customThe reaction was quenched with water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe filtrated was evaporated in vacuo
  6. customthe crude product was purified by silica gel flash chromatography
  7. washeluting with 33% hexanes in ethyl acetate

出典と根拠

ORDレコード
ord-cf148fde9f764380ad171f6e31aa055e
出典データセット
uspto-grants-2006_12
特許番号
US07144881B2

反応ノート

読み込み中…