Thionyl Chloride → HCID 18762821, compound

HRID 431017Notes

Reaction equation

HRID 431017 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:19][C:20]([CH3:22])=[O:21])=[C:9]([O:12][CH2:13][CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:10]=2)[N:5]=[CH:4][N:3]=1.S(Cl)([Cl:25])=O>CN(C)C=O>[Cl:25][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:19][C:20]([CH3:22])=[O:21])=[C:9]([O:12][CH2:13][CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 178475247HCID 178475247, compound

Product 1

HCID 18762821HCID 18762821, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

3.80 g of 4-hydroxy-6-cyclopentylmethoxy-7-methylcarbonyloxy-quinazoline are suspended in 90 ml thionyl chloride and heated to boiling under a nitrogen atmosphere. After the addition of four drops of N,N-dimethylformamide the reaction mixture is refluxed for a further two hours. After cooling to ambient temperature the excess thionyl chloride is distilled off in a water jet vacuum. The brown residue is stirred with 30 ml toluene. The solvent is distilled off, leaving 4.30 g of a greyish-brown solid, which is reacted further without any more purification.

Workup

  1. temperatureheated
  2. temperatureis refluxed for a further two hours
  3. distillationis distilled off in a water jet vacuum
  4. distillationThe solvent is distilled off

Sources & evidence

ORD record
ord-2a1dc6db6a4d4922bc49707ddffcafd2
Source dataset
uspto-grants-2003_12
Patent number
US06656946B2

Reaction notes

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