Pyridine → 3-(N-Acetylcarbamoyl)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol hemihydrate

HRID 2164282노트

반응식

HRID 2164282 반응식
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([CH2:8][C:9]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])([OH:16])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1)(=[O:7])[NH2:6].N1C=CC=CC=1>C(#N)C>[OH2:3].[C:1]([NH:6][C:5]([CH2:8][C:9]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])([OH:16])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1)=[O:7])(=[O:3])[CH3:2].[C:1]([NH:6][C:5]([CH2:8][C:9]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])([OH:16])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1)=[O:7])(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 136030731-Carbamoyl-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol

생성물 1

HCID 704255333-(N-Acetylcarbamoyl)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol hemihydrate수율 19%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

A solution of acetyl chloride (0.12 g, 1.5 mmole) in dry acetonitrile (2 ml) was added dropwise to a stirred solution of 3-carbamoyl-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (0.314 g., 1 mmole) and pyridine (0.12 g., 1.5 mmole) in dry acetonitrile (2 ml) at -20° C. The solution was allowed to warm to room temperature and was stirred at room temperature for a further 18 hours. The solvent was then removed under reduced pressure and the residue was partitioned between water (10 ml) and chloroform (40 ml). The organic phase was separated, dried over MgSO4 and evaporated. The residue was chromatographed on silica eluting with 10:1 (v:v) chloroform/methanol and the fractions containing the product were combined, evaporated, and recrystallized from diisopropyl ether to furnish the title compound, (67 mg., 19%), m.p. 148°-150° C.

후처리

  1. customThe solvent was then removed under reduced pressure
  2. customthe residue was partitioned between water (10 ml) and chloroform (40 ml)
  3. customThe organic phase was separated
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was chromatographed on silica eluting with 10:1 (v:v) chloroform/methanol
  7. additionthe fractions containing the product
  8. customevaporated
  9. customrecrystallized from diisopropyl ether

출처 및 근거

ORD 기록
ord-fa5a6b848e2c43779697ce275706b117
출처 데이터셋
uspto-grants-1985_03
특허 번호
US04503063

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