Dimethylformamide → 7-(Benzyloxy)-4-chloroquinazoline

HRID 454085ノート

反応式

HRID 454085 の反応式
[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

参加物

4

反応物 3

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

生成物 1

HCID 220309237-(Benzyloxy)-4-chloroquinazoline収率 89%

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-d13674a1f50940ca8b287a6be7ce52c7
出典データセット
uspto-grants-2013_07
特許番号
US08492560B2

反応ノート

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