Chloroform → 3-cyclopropyl-2-(4-methoxy-phenyl)-3H-imidazole-4-carbaldehyde

HRID 732103노트

반응식

HRID 732103 반응식
[CH:1]1([NH:4][C:5](=[NH:14])[C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.Br[C:16](=[CH:19]OC(C)C)[CH:17]=[O:18].C([O-])([O-])=O.[K+].[K+].C(Cl)(Cl)Cl>O>[CH:1]1([N:4]2[C:16]([CH:17]=[O:18])=[CH:19][N:14]=[C:5]2[C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)[CH2:2][CH2:3]1

참가 물질

6

반응물 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 534166342-Bromo-3-isopropoxy-propenalHCID 178491237HCID 178491237, 화합물

생성물 1

HCID 578380093-cyclopropyl-2-(4-methoxy-phenyl)-3H-imidazole-4-carbaldehyde수율 85%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

N-cyclopropyl-4-methoxy-benzamidine (0.90 g, 4.75 mmol), 2-bromo-3-isopropoxy-propenal (1.37 g, 7.12 mmol) and K2CO3 (0.98 g, 7.12 mmol) were mixed with chloroform (10 ml) and water (1.2 ml), followed by stirring at r.t. for 24 h. After drying of the reaction mixture (Na2SO4), filtration and concentration of the filterate in-vacuo, the crude residue was purified via flash chromatography (40% EA in hex.) to isolate the title compound (973 mg, 85%). 1H-NMR: 9.83 (s, 1H), 7.82 (m, 3H), 7.02 (d, 2H), 3.89 (s, 3H), 3.58 (m, 1H), 1.13 (m, 2H), 0.64 (m, 2H).

후처리

  1. dry with materialAfter drying of the reaction mixture (Na2SO4), filtration and concentration of the filterate in-vacuo
  2. customthe crude residue was purified via flash chromatography (40% EA in hex.)

출처 및 근거

ORD 기록
ord-59d3df64d5184e9fb6ce967002974f67
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585881B2

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