Thionyl Chloride → HCID 178481267, compound

HRID 903548Notes

Reaction equation

HRID 903548 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7]([NH:13][CH2:14][CH2:15][CH2:16]O)=[N:6][CH:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.S(Cl)([Cl:26])=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7]([NH:13][CH2:14][CH2:15][CH2:16][Cl:26])=[N:6][CH:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178481274HCID 178481274, compound

Product 1

HCID 178481267HCID 178481267, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 3.3 g of 6-chloro-1,4-dihydro-2-(γ-hydroxypropylamino)-1-methyl-4-phenylquinazoline, 3.6 g of thionyl chloride and 50 ml of chloroform was stirred at room temperature overnight, and refluxed for an additional 2 hours. The reaction mixture was concentrated to dryness under reduced pressure to give 3.5 g of 6-chloro-1,4-dihydro-2-(γ-chloropropylamino)-1-methyl-4-phenylquinazoline as a residue. To the residue were added 100 ml of dry ethanol and 2.8 g of potassium carbonate and the resulting mixture was heated under reflux for 5 hours. After cooling, insoluble material was filtered off and the filtrate was concentrated to dryness. The residue was chromatographed on activated alumina using chloroform as an eluent to give 8-chloro-11-methyl-6-phenyl-3,4,6,11-tetrahydro-2H-pyrimido[2,1-b]quinazoline.

Workup

  1. temperaturerefluxed for an additional 2 hours
  2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-122f025299b5486f9774ae326e7c91c4
Source dataset
uspto-grants-1980_10
Patent number
US04228167

Reaction notes

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