Thionyl Chloride → HCID 57979822, compound

HRID 1867719Notes

Reaction equation

HRID 1867719 reaction equation
[Cl:1][C:2]1[C:3]([F:23])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([CH2:19]O)[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.S(Cl)([Cl:26])=O>>[Cl:1][C:2]1[C:3]([F:23])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([CH2:19][Cl:26])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 57979865{4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methanol

Product 1

HCID 57979822HCID 57979822, compoundYield 100%

Procedure

{4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methanol (0.20 g, 0.604 mmol) was added to neat thionyl chloride (1 ml) over a period of 5 minutes. The resulting solution was stirred for 30 minutes, concentrated to dryness and the residue was subjected to an azeotropic distillation with toluene (2×10 ml). The resulting solid was triturated with acetonitrile (5 ml) filtered and dried to a constant weight in a vacuum oven at 40° C. to give the hydrochloride salt of N-(3-chloro-2-fluorophenyl)-6-(chloromethyl)-7-methoxyquinazolin-4-amine (0.21 g, 100%) as a white solid; Mass Spectrum: (M+H)+ 352.

Workup

  1. concentrationconcentrated to dryness
  2. distillationthe residue was subjected to an azeotropic distillation with toluene (2×10 ml)
  3. customThe resulting solid was triturated with acetonitrile (5 ml)
  4. filtrationfiltered
  5. customdried to a constant weight in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-effcb9692b9a44ab821b3bbd4ddb1e07
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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