Dimethylformamide → Phenobarbital

HRID 1658881노트

반응식

HRID 1658881 반응식
[CH3:1][CH2:2][C:3]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9](=[O:10])[N:8]=[C:7]([O-:11])[NH:6][C:4]1=[O:5].[Na+].ClCC([O-])=O.[Na+].[Cl-].[Cl-].[Ca+2].CN(C=O)C>CO>[CH3:1][CH2:2][C:3]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:9](=[O:10])[NH:8][C:7](=[O:11])[NH:6][C:4]1=[O:5]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 5284359Calcium ChlorideHCID 23665759Sodium chloroacetateHCID 23674889Phenobarbital sodium

생성물 1

HCID 4763Phenobarbital수율 36.9%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

A solution of sodium phenobarbitone (8.8 g, 35 mmoles), and sodium chloroacetate (4.5 g, 38 mmoles) in methanol (250 ml) was mixed with a solution of CaCl2 (3 g) in methanol (50 ml). After addition of 5 ml DMF the mixture was refluxed for 36 hours. After removal of the solvent, the residue was treated with water (100 ml) and acidified with conc. HCl followed by extraction with chloroform. The organic layer was evaporated to dryness and the residue treated with 10% NaHCO3 solution. Extraction with chloroform and evaporation of the organic layer yielded 3 g of unreacted phenobarbital. The bicarbonate layer was acidified with conc. HCl and extracted with chloroform. Evaporation of the dried (MgSO4) chloroform yielded 4.5 g of a gummy material which solidified slowly on standing. TLC and NMR showed this to be nearly pure monoacid with only traces of unreacted phenobarbitone and dialkylated derivative.

후처리

  1. temperaturewas refluxed for 36 hours
  2. customAfter removal of the solvent
  3. additionthe residue was treated with water (100 ml)
  4. extractionfollowed by extraction with chloroform
  5. customThe organic layer was evaporated to dryness
  6. additionthe residue treated with 10% NaHCO3 solution
  7. extractionExtraction
  8. customwith chloroform and evaporation of the organic layer

출처 및 근거

ORD 기록
ord-3aa01259f1e54672891c1ba34032acac
출처 데이터셋
uspto-grants-1976_06
특허 번호
US03966744

반응 노트

불러오는 중…