Dimethylformamide → 7-(Benzyloxy)-4-chloro-6-methoxyquinazoline

HRID 1791524Notes

Reaction equation

HRID 1791524 reaction equation
[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][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.S(Cl)([Cl:29])=O>>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:29])=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1354047187-Benzyloxy-6-methoxy-3H-quinazolin-4-one

Product 1

HCID 106619987-(Benzyloxy)-4-chloro-6-methoxyquinazoline

Procedure

7-Benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (20.3 g, 124 mmol), (prepared as described for the starting material in Example 1), was taken up in thionyl chloride (440 ml) and DMF (1.75 ml) then heated at reflux for 4 hours. The thionyl chloride was evaporated under vacuum and the residue azeotroped with toluene three times to give 7-benzyloxy-4-chloro-6-methoxyquinazoline.

Workup

  1. temperatureat reflux for 4 hours
  2. customThe thionyl chloride was evaporated under vacuum
  3. customthe residue azeotroped with toluene three times

Sources & evidence

ORD record
ord-6e4a2e6d07af474dba1790077b8de6ed
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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