Sulfuric Acid → 1-(3-n-Butoxy-2-hydroxypropyl)-5-ethyl-5-phenyl-(1H,3H,5H)-pyrimidine-2,4,6-trione

HRID 257406

반응식

HRID 257406 반응식
[CH3:1][CH2:2][C:3]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:10](=[O:11])[NH:9][C:7](=[O:8])[NH:6][C:4]1=[O:5].C(N(CC)CC)C.Cl[CH2:26][CH:27]([OH:34])[CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH3:33].S(=O)(=O)(O)O>CN(C)C=O>[CH2:30]([O:29][CH2:28][CH:27]([OH:34])[CH2:26][N:6]1[C:4](=[O:5])[C:3]([CH2:2][CH3:1])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10](=[O:11])[NH:9][C:7]1=[O:8])[CH2:31][CH2:32][CH3:33]

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 4763PhenobarbitalHCID 8471TriethylamineHCID 277592-Propanol, 1-butoxy-3-chloro-

생성물 1

HCID 197831241-(3-n-Butoxy-2-hydroxypropyl)-5-ethyl-5-phenyl-(1H,3H,5H)-pyrimidine-2,4,6-trione수율 53.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of phenobarbital (69.6 g, 0.3 mole) in dimethylformamide (60 ml) containing triethylamine (20.2 g, 0.2 mole) was stirred with 1-chloro-3-n-butoxy-2-propanol (33.2 g, 0.2 mole) for 6 hours at 70° C. The reaction mixture was then poured into 3% sulphuric acid (500 ml) and the precipitated product was extracted with toluene (200 ml) at 70° C. The toluene layer was separated, washed with 3% aqueous sulphuric acid (200 ml) and left overnight at 4° C. The precipitated phenobarbital was filtered off and filtrate extracted with 5% aqueous sodium carbonate (5×100 ml). The organic layer was then extracted with 1M aqueous sodium hydroxide (2×200 ml), the aqueous layers collected, washed with toluene (100 ml) and the pH was adjusted to 3 with sulphuric acid. The precipitated product was extracted with toluene (150 ml), the organic layer was separated, dried and evaporated under reduced pressure to give the title compound (38.5 g, 53%); purity by HPLC 96.5% .

후처리

  1. extractionthe precipitated product was extracted with toluene (200 ml) at 70° C
  2. customThe toluene layer was separated
  3. washwashed with 3% aqueous sulphuric acid (200 ml)
  4. filtrationThe precipitated phenobarbital was filtered off
  5. extractionfiltrate extracted with 5% aqueous sodium carbonate (5×100 ml)
  6. extractionThe organic layer was then extracted with 1M aqueous sodium hydroxide (2×200 ml)
  7. customthe aqueous layers collected
  8. washwashed with toluene (100 ml)
  9. extractionThe precipitated product was extracted with toluene (150 ml)
  10. customthe organic layer was separated
  11. customdried
  12. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-e726e6ac9f05453f95faec9db4973de4
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05262402

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