Triethylamine → 2-(2-chlorophenyl)-1-(4-chlorophenyl)-N-methoxy-N-methyl-1H-imidazole-4-carboxamide

HRID 1062438

반응식

HRID 1062438 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH:10]=[C:11]([C:13](Cl)=[O:14])[N:12]=1.Cl.[CH3:24][NH:25][O:26][CH3:27].C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH:10]=[C:11]([C:13]([N:25]([O:26][CH3:27])[CH3:24])=[O:14])[N:12]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 222853742-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carbonyl chloride

생성물 1

HCID 222855752-(2-chlorophenyl)-1-(4-chlorophenyl)-N-methoxy-N-methyl-1H-imidazole-4-carboxamide수율 83%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carbonyl chloride (4.71 g, 13.4 mmol, prepared by the method described in Example 13, step 1) in 10 mL dichloromethane was added to a solution of N,O-dimethylhydroxyamine hydrochloride (1.44 g, 14.7 mmol) and triethylamine (5.6 mL, 40.2 mmol) in 60 mL dichloromethane in an ice water bath under argon with stirring. The bath was removed upon completion of addition. Stirring was continued for 1 h. Water was added and the mixture was extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated down under reduced pressure. The crude product was purified on silica gel, eluting with ethyl acetate to yield 2-(2-chlorophenyl)-1-(4-chlorophenyl)-N-methoxy-N-methyl-1H-imidazole-4-carboxamide as an off-white solid (4.20 g, 83%): Rf=0.22 (ethyl acetate).

후처리

  1. customThe bath was removed upon completion of addition
  2. stirringStirring
  3. additionWater was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated down under reduced pressure
  7. customThe crude product was purified on silica gel
  8. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-139525904f2c4ae597c1ab385f81bdf3
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960601B2

연결된 노트

불러오는 중…