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

HRID 2117845노트

반응식

HRID 2117845 반응식
[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]

참가 물질

8

반응물 4

HCID 11776TriphenylphosphineHCID 660114-Nitrobenzyl bromideHCID 21914786HCID 21914786, 화합물HCID 23699084Potassium butoxide

생성물 1

HCID 219151012-methyl-N-{4-[(E)-2-(4-nitrophenyl)ethenyl]-1,3-thiazol-2-yl}propanamide수율 6.4%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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 (36.0 mg).

후처리

  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

출처 및 근거

ORD 기록
ord-7838ac90fc46464f86ce5973f92f5652
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07442715B2

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