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Water → tert-Butyl 2-(4-(1H-benzo[d]imidazol-2-yl)phenyl)morpholine-4-carboxylate

HRID 710234
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HRID 710234 반응식
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)=[CH:5][CH:4]=1)=O.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH2:29].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].O>CC(N(C)C)=O>[NH:22]1[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N:29]=[C:1]1[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)=[CH:5][CH:4]=1
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6

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HCID 962WaterHCID 7243O-PhenylenediamineHCID 656671Sodium PyrosulfiteHCID 87320997Tert-butyl 2-(4-formylphenyl)morpholine-4-carboxylate

생성물 1

HCID 131733926tert-Butyl 2-(4-(1H-benzo[d]imidazol-2-yl)phenyl)morpholine-4-carboxylate수율 85.2%

시약·촉매·용매 1

HCID 31374
Dimethylacetamide
용매

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온도
90 °C

실험 절차

tert-Butyl 2-(4-formylphenyl)morpholine-4-carboxylate (300 mg, 1.03 mmol) was dissolved in dimethylacetamide (4.5 ml). 1,2-Diaminobenzene (134 mg, 1.24 mmol) and sodium metabisulfite (294 mg, 1.54 mmol) were added and the reaction mixture was stirred at 90° C. overnight. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over MgSO4 and evaporated. The crude material was purified by flash chromatography (20 g silica gel, 40 to 70% ethyl acetate in heptane) to yield a white solid (333 mg, 85%). MS (ISP): 280.3 (100%, [M-BOC+H]+), 380.2 (20%, [M+H]+).

후처리

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated
  5. customThe crude material was purified by flash chromatography (20 g silica gel, 40 to 70% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-3f9f9993d34543faab8c9271b21f29fd
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09181230B2

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