Dimethylformamide → 7-(Benzyloxy)-4-chloroquinazoline

HRID 454085노트

반응식

HRID 454085 반응식
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=O)[NH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.S(Cl)([Cl:27])=O>>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:27])=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1357631107-(Benzyloxy)-3,4-dihydroquinazolin-4-one

생성물 1

HCID 220309237-(Benzyloxy)-4-chloroquinazoline수율 89%

실험 절차

A mixture of 7-benzyloxy-3,4-dihydroquinazolin-4-one (11 g, 43.6 mmol) and DMF (1 ml) in thionyl chloride (100 ml) was heated at reflux for 1.5 hours. Excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene. The residue was partitioned between methylene chloride and water and saturated aqueous sodium hydrogen carbonate was added until the aqueous layer was at about pH9. The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated to give 7-benzyloxy-4-chloroquinazoline (10.5 g, 89%).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. customExcess thionyl chloride was removed by evaporation
  4. customthe residue azeotroped with toluene
  5. customThe residue was partitioned between methylene chloride and water and saturated aqueous sodium hydrogen carbonate
  6. additionwas added until the aqueous layer
  7. customThe organic layer was separated
  8. washwashed with water, brine
  9. dry with materialdried (MgSO4)
  10. customevaporated

출처 및 근거

ORD 기록
ord-d13674a1f50940ca8b287a6be7ce52c7
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492560B2

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