Triphenylphosphine → 2-methyl-N-{4-[(E)-2-(4-nitrophenyl)ethenyl]-1,3-thiazol-2-yl}propanamide

HRID 1246435ノート

反応式

HRID 1246435 の反応式
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O-]CCCC.[K+].[CH:37]([C:39]1[N:40]=[C:41]([NH:44][C:45](=[O:49])[CH:46]([CH3:48])[CH3:47])[S:42][CH:43]=1)=O>O.C(OCC)(=O)C.CN(C)C=O>[CH3:47][CH:46]([CH3:48])[C:45]([NH:44][C:41]1[S:42][CH:43]=[C:39](/[CH:37]=[CH:8]/[C:7]2[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[N:40]=1)=[O:49]

参加物

8

反応物 4

HCID 11776TriphenylphosphineHCID 660114-Nitrobenzyl bromideHCID 21914786HCID 21914786、化合物HCID 23699084Potassium butoxide

生成物 1

HCID 219151012-methyl-N-{4-[(E)-2-(4-nitrophenyl)ethenyl]-1,3-thiazol-2-yl}propanamide収率 64.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 4-nitrobenzyl bromide (381 mg), triphenylphosphine (463 mg) and N,N-dimethylformamide (3 ml) was stirred for 5 hours at room temperature. To the mixture were added potassium butoxide (238 mg) and then N-(4-formyl-1,3-thiazol-2-yl)-2-methylpropanamide (350 mg), and the mixture was stirred for 13 hours at the same temperature. The reaction mixture was poured into ethyl acetate (20 ml) and water (20 ml). The organic layer was washed with water (20 ml), dried over sodium sulfate and concentrated in vacuo. The crystalline residue was collected and washed to give 2-methyl-N-{4-[(E)-2-(4-nitrophenyl)ethenyl]-1,3-thiazol-2-yl}propanamide (360 mg).

後処理

  1. washThe organic layer was washed with water (20 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crystalline residue was collected
  5. washwashed

出典と根拠

ORDレコード
ord-20e14730fa934a41b1049b758eec4418
出典データセット
uspto-grants-2006_10
特許番号
US07125901B2

反応ノート

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