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

HRID 2164283ノート

反応式

HRID 2164283 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e37a14225bfb4fd5b382067a9ed920df
出典データセット
uspto-grants-1985_03
特許番号
US04503063

反応ノート

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