Epichlorohydrin → 4-(2,3-Epoxypropoxy)benzamide

HRID 488931노트

반응식

HRID 488931 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[CH2:11]([CH:13]1[O:15][CH2:14]1)Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:15]1[CH2:14][CH:13]1[CH2:11][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 650524-Hydroxybenzamide

생성물 1

HCID 122382474-(2,3-Epoxypropoxy)benzamide수율 28.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

To a sealed tube was added 4-hydroxybenzamide (200 mg, 1.458 mmol), epichlorohydrin (135 mg, 1.458 mmol) and potassium carbonate (403 mg, 2.916 mmol) in 7 mL of dry DMF. The reaction mixture was stirred at 70° C. for 18 h. The reaction mixture was filtered and concentrated. The residue was purified by flash chromatography, eluting with 0-5% 2M NH3 in MeOH/CH2Cl2. The product fractions were collected and concentrated to afford 80 mg of 4-oxiranylmethoxy-benzamide as a white solid.

후처리

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography
  4. washeluting with 0-5% 2M NH3 in MeOH/CH2Cl2
  5. customThe product fractions were collected
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d02968bde21b4c65bfee35e12ba4962b
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06974870B2

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