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

HRID 453981Notes

Reaction equation

HRID 453981 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 (35 g, 124 mmol) was suspended in thionyl chloride (440 ml) and DMF (1.75 ml) and heated at reflux for 4 hours. The thionyl chloride was evaporated under vacuum and the residue azeotroped with toluene three times. The residue was dissolved in NMP (250 ml) to give a solution of 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
  4. dissolutionThe residue was dissolved in NMP (250 ml)

Sources & evidence

ORD record
ord-32a290c4c8b0495f87345ad18bc45b69
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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