Butyric Acid → 4'-Hydroxybutyranilide

HRID 503664

반응식

HRID 503664 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9](O)(=[O:13])[CH2:10][CH2:11][CH3:12].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:9]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1)(=[O:13])[CH2:10][CH2:11][CH3:12]

참가 물질

6

반응물 3

HCID 264Butyric AcidHCID 4034-AminophenolHCID 10868Dicyclohexylcarbodiimide

생성물 1

HCID 668744'-Hydroxybutyranilide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

4-aminophenol (550 mg; 5 mmol) is added to a solution of butyric acid (1.4 mL; 15 mmol) in DCM (20 mL) at room temperature and stirred vigorously. To this solution DCC (2.48 g; 12 mmol) is added followed by DMAP (24 mg) and the contents stirred overnight at room temperature. The reaction mixture is then filtered and washed with DCM. The filtrate is concentrated and redissolved in methanol, added with 10% aqueous sodium bicarbonate solution and stirred vigorously until diacylated byproduct disappeared (as detected by LC-MS) to yield 4-butyramidophenol as the only product. The product was used for further transformation without further purification.

후처리

  1. stirringthe contents stirred overnight at room temperature
  2. filtrationThe reaction mixture is then filtered
  3. washwashed with DCM
  4. concentrationThe filtrate is concentrated
  5. dissolutionredissolved in methanol
  6. additionadded with 10% aqueous sodium bicarbonate solution
  7. stirringstirred vigorously until diacylated byproduct

출처 및 근거

ORD 기록
ord-ac6353b317e04aec904eccd77aa26a4e
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776919B2

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