Dicyclohexylcarbodiimide → 2-cyclobutylidene-N-(4-methoxy-2,3-dimethylphenyl)acetamide

HRID 2103084

반응식

HRID 2103084 반응식
[C:1]1(=[CH:5][C:6]([OH:8])=O)[CH2:4][CH2:3][CH2:2]1.[CH3:9][C:10]1[C:11]([O:18][CH3:19])=[CH:12][CH:13]=[C:14]([C:16]=1[CH3:17])[NH2:15].CN(C)CCCN=C=NCC.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl.C(N(CC)CC)C>[C:1]1(=[CH:5][C:6]([NH:15][C:14]2[CH:13]=[CH:12][C:11]([O:18][CH3:19])=[C:10]([CH3:9])[C:16]=2[CH3:17])=[O:8])[CH2:2][CH2:3][CH2:4]1

참가 물질

8

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 110948094-Methoxy-2,3-dimethylanilineHCID 219231732-Cyclobutylideneacetic acid

생성물 1

HCID 690533272-cyclobutylidene-N-(4-methoxy-2,3-dimethylphenyl)acetamide수율 65.3%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

Cyclobutylideneacetic acid (3.8 g), 5,6-dimethyl-4-methoxyaniline (5 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDC) (4.7 g), 1,3-dicyclohexylcarbodiimide (DCC) (2.4 g), 4-dimethylaminopyridine (DMAP) (805 mg) and triethylamine (TEA) (7.3 g) were dissolved in dichloromethane (80 mL). The mixture was stirred at room temperature overnight, concentrated, and the residue dissolved in ethyl acetate. The organic phase was washed with water (3×20 mL) and 1M HCl (3×20 mL), and a white solid was filtered out. The organic solution was then dried out by evaporation giving 2-cyclobutylidene-N-(4-methoxy-2,3-dimethylphenyl)acetamide as a brown solid (5.3 g). The product was used in the next step without further purification. MS: (m/z)=246 (100, M+H+).

후처리

  1. concentrationconcentrated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe organic phase was washed with water (3×20 mL) and 1M HCl (3×20 mL)
  4. filtrationa white solid was filtered out
  5. customThe organic solution was then dried out by evaporation

출처 및 근거

ORD 기록
ord-e76f5d88b4074044a32e6ad90da2d763
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576094B2

연결된 노트

불러오는 중…