Thionyl Chloride → HCID 19392211, compound

HRID 1648212Notes

Reaction equation

HRID 1648212 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[NH:7][C:8]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)=[N:9]2)=[CH:4][CH:3]=1.S(Cl)([Cl:21])=O>>[ClH:21].[Cl:21][C:6]1[C:5]2[C:10](=[CH:11][C:2]([F:1])=[CH:3][CH:4]=2)[N:9]=[C:8]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 135449047HCID 135449047, compound

Product 1

HCID 19392211HCID 19392211, compound

Procedure

A suspension of the quinazolinone compound (1.2 g, prepared in Reference example 4) in 20 mL of thionyl chloride was heated to reflux for three hours. The excess of thionyl chloride was removed by distillation. The residue was distilled azeotropically with benzene (5 mL×3) and then reduced the total volume to about 5 mL. After cooling in refrigerator, precipitate was collected by filtration and washed with benzene twice to give the title compound (1.38 g) as a crystalline solid having the following physical data.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for three hours
  3. customThe excess of thionyl chloride was removed by distillation
  4. distillationThe residue was distilled azeotropically with benzene (5 mL×3)
  5. temperatureAfter cooling in refrigerator, precipitate
  6. filtrationwas collected by filtration
  7. washwashed with benzene twice

Sources & evidence

ORD record
ord-23529d577e8548d7a34c231efd1f2e94
Source dataset
uspto-grants-1995_07
Patent number
US05436233

Reaction notes

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