Dimethylformamide → 7-(Benzyloxy)-4-chloroquinazoline

HRID 639964Notes

Reaction equation

HRID 639964 reaction equation
CN(C)C=O.[CH2:6]([O:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18](=O)[NH:19][CH:20]=[N:21]2)=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.S(Cl)([Cl:27])=O>>[CH2:6]([O:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18]([Cl:27])=[N:19][CH:20]=[N:21]2)=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

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

Product 1

HCID 220309237-(Benzyloxy)-4-chloroquinazolineYield 86.5%

Procedure

Dimethylformamide (0.5 ml) was added to a suspension of 7-(benzyloxy)quinazolin-4-(3H)-one (5.04 g, 20 mmol) in thionyl chloride (50 ml) and the mixture heated at reflux for 2 hours. The thionyl chloride was removed in vacuo and the residual oil dissolved in dichloromethane (100 ml). This solution was slowly added to an aqueous saturated solution of sodium bicarbonate (100 ml) and the organic phase recovered. The aqueous phase was extracted with dichloromethane (2×50 ml) and the combined organics dried and concentrated to yield 7-(benzyloxy)-4-chloroquinazoline (4.68 g, 86.5% yield):

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 2 hours
  3. customThe thionyl chloride was removed in vacuo
  4. dissolutionthe residual oil dissolved in dichloromethane (100 ml)
  5. additionThis solution was slowly added to an aqueous saturated solution of sodium bicarbonate (100 ml)
  6. customthe organic phase recovered
  7. extractionThe aqueous phase was extracted with dichloromethane (2×50 ml)
  8. customthe combined organics dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-4698f4b36e6e4f409dbeecfcb95d0a52
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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