Methyl chloroformate → 2-(2,4-Dichlorophenyl)-3-(N,N-dimethoxycarbonylcarbamoyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol

HRID 2164283노트

반응식

HRID 2164283 반응식
[C:1]([CH2:4][C:5]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])([OH:12])[CH2:6][N:7]1[CH:11]=[N:10][CH:9]=[N:8]1)(=[O:3])[NH2:2].[H-].[Na+].Cl[C:24]([O:26][CH3:27])=[O:25]>O1CCCC1>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[C:5]([OH:12])([CH2:4][C:1](=[O:3])[N:2]([C:24]([O:26][CH3:27])=[O:25])[C:24]([O:26][CH3:27])=[O:25])[CH2:6][N:7]1[CH:11]=[N:10][CH:9]=[N:8]1

참가 물질

5

반응물 3

HCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 136030731-Carbamoyl-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol

생성물 1

HCID 204060752-(2,4-Dichlorophenyl)-3-(N,N-dimethoxycarbonylcarbamoyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol수율 5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

3-Carbamoyl-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (0.94 g., 3 mmole) was added to a suspension of oil-free sodium hydride (0.14 g., 5.8 mmole) in dry tetrahydrofuran (10 ml). The suspension was stirred for one hour and then a solution of methyl chloroformate (0.6 g., 6.3 mmole) in dry tetrahydrofuran (10 ml) was added dropwise over 15 minutes. The mixture was stirred at room temperature for three hours and then the solvent was evaporated in vacuo. The residue was partitioned between saturated aqueous sodium bicarbonate solution (10 ml) and ethyl acetate (40 ml), and the organic phase was separated, washed with brine (10 ml), dried (MgSO4) and evaporated. The residue was chromatographed on silica eluting with ethyl acetate/methanol 95:5 (v:v), and the fractions containing the product were combined and evaporated and recrystallized from ethyl acetate-hexane to give the title compound, (62 mg, 5%), m.p. 155°-156° C.

후처리

  1. stirringThe mixture was stirred at room temperature for three hours
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was partitioned between saturated aqueous sodium bicarbonate solution (10 ml) and ethyl acetate (40 ml)
  4. customthe organic phase was separated
  5. washwashed with brine (10 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was chromatographed on silica eluting with ethyl acetate/methanol 95:5 (v:v)
  9. additionthe fractions containing the product
  10. customevaporated
  11. customrecrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-e37a14225bfb4fd5b382067a9ed920df
출처 데이터셋
uspto-grants-1985_03
특허 번호
US04503063

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