Phosphorus oxychloride → HCID 17976094, compound

HRID 346975Notes

Reaction equation

HRID 346975 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18](=[O:26])[C:19]4[CH:24]=[CH:23][C:22]([I:25])=[CH:21][CH:20]=4)[CH:16]=3)[NH:11][C:10](=O)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.P(Cl)(Cl)([Cl:30])=O>>[Cl:30][C:10]1[N:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:19]3[CH:24]=[CH:23][C:22]([I:25])=[CH:21][CH:20]=3)=[O:26])[CH:16]=2)[N:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 21082043HCID 21082043, compound

Product 1

HCID 17976094HCID 17976094, compoundYield 82%

Procedure

A mixture of intermediate (38) (0.0103 mol) in phosphoryl chloride (20 ml) was stirred and refluxed for 1 hour. The mixture was cooled to room temperature and evaporated till dryness. The residue was taken up in DCM. This solution was poured out into ice/NH4OH and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue (5.3 g) was crystallized from 2-propanone/DIPE. The precipitate was filtered off and dried, yielding 4.25 g (82%) of [2-chloro-4-(3-chlorophenyl)-6-quinazolinyl](4-iodophenyl)-methanone, mp. 153° C. (intermediate 39).

Workup

  1. temperaturerefluxed for 1 hour
  2. customevaporated till dryness
  3. additionThis solution was poured out into ice/NH4OH
  4. extractionextracted with DCM
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue (5.3 g) was crystallized from 2-propanone/DIPE
  10. filtrationThe precipitate was filtered off
  11. customdried

Sources & evidence

ORD record
ord-3e3ccbe334fc482f8a9b3bcecce89fea
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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