Acetic Anhydride → N-(4-ethoxy-3-fluorophenyl)acetamide

HRID 1620298노트

반응식

HRID 1620298 반응식
[CH2:1]([O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][C:5]=1[F:11])[CH3:2].CCN(C(C)C)C(C)C.[C:21](OC(=O)C)(=[O:23])[CH3:22]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([O:3][C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:21](=[O:23])[CH3:22])=[CH:6][C:5]=1[F:11])[CH3:2]

참가 물질

6

반응물 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 195992054-Ethoxy-3-fluoroaniline2회

생성물 1

HCID 68182197N-(4-ethoxy-3-fluorophenyl)acetamide수율 41%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 4-ethoxy-3-fluoroaniline SMA 44094 (464 mg, 2.99 mmol) in dry CH2Cl2 (15 mL) in a 50 mL round-bottomed flask equipped with a magnetic stirrer were added DIEA (2.0 mL, 12 mmol), DMAP (87 mg, 0.7 mmol) and acetic anhydride (1.7 mL, 18 mmol) and the mixture was stirred for 5 h at RT. The solution was then diluted with more CH2Cl2 (30 mL), washed with brine (10 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum. Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 50:50) gave N-(4-ethoxy-3-fluorophenyl)acetamide SMA 44098 as a beige solid (242 mg, 41% yield).

후처리

  1. washwashed with brine (10 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated at 40° C. under vacuum
  5. customPurification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 50:50)

출처 및 근거

ORD 기록
ord-4738c540d8bc4e64aee4d8784a57fda2
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772316B2

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