Dimethylformamide → 4-Chloro-2-[(3-phenyl)phenyl]-7-methoxyquinazolin-6-yl acetate

HRID 1406967ノート

反応式

HRID 1406967 の反応式
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[C:10]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:18]=1)[NH:9][C:8]2=O)(=[O:3])[CH3:2].CN(C=O)C.O=S(Cl)[Cl:37]>>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[C:10]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:18]=1)[N:9]=[C:8]2[Cl:37])(=[O:3])[CH3:2]

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1362032482-[(3-Phenyl)phenyl]-7-methoxy-4-oxo-3,4-dihydroquinazolin-6-yl acetate

生成物 1

HCID 593618554-Chloro-2-[(3-phenyl)phenyl]-7-methoxyquinazolin-6-yl acetate

実験手順

To a mixture of 2-[(3-phenyl)phenyl]-7-methoxy-4-oxo-3,4-dihydroquinazolin-6-yl acetate (3.6 g, 9.32 mmole) in SOCl2 (40 mL) was added DMF (1 mL) and the reaction was stirred at reflux for 16 h. The mixture was cooled to RT and then the volatiles were removed in vacuo. The crude product was dissolved in CHCl3 (300 mL) and washed with saturated NaHCO3 solution (3×150 mL), water (2×150 mL) and brine (1×150 mL) and dried with Na2SO4. The solution was concentrated in vacuo to yield 4-chloro-2-[(3-phenyl)phenyl]-7-methoxyquinazolin-6-yl acetate (4.0 g, 9.88 mmole). HPLC retention time 11.12 mins. (5-95-13 method).

後処理

  1. temperatureat reflux for 16 h
  2. customthe volatiles were removed in vacuo
  3. dissolutionThe crude product was dissolved in CHCl3 (300 mL)
  4. washwashed with saturated NaHCO3 solution (3×150 mL), water (2×150 mL) and brine (1×150 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationThe solution was concentrated in vacuo

出典と根拠

ORDレコード
ord-4aefa7f4352649eeab5f9aab6bec8cce
出典データセット
uspto-grants-2014_12
特許番号
US08916576B2

反応ノート

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