Acetic Anhydride → 4-(4-Chloro-3-formamidobenzyl)amino-6-chloroquinazoline

HRID 1003525Notes

Reaction equation

HRID 1003525 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[N:10]=[CH:9][N:8]=1.[C:22](OC(=O)C)(=[O:24])C>C(O)=O>[Cl:21][C:20]1[CH:19]=[CH:18][C:4]([CH2:5][NH:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=3)[N:10]=[CH:9][N:8]=2)=[CH:3][C:2]=1[NH:1][CH:22]=[O:24]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 187967134-(3-Amino-4-chlorobenzyl)amino-6-chloroquinazoline

Product 1

HCID 187966694-(4-Chloro-3-formamidobenzyl)amino-6-chloroquinazolineYield 65%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

0.90 g (2.82 mmol) of the 4-(3-amino-4-chlorobenzyl)amino-6-chloroquinazoline prepared in Example 147 was dissolved in 15 ml of formic acid, followed by the addition of 1 ml of acetic anhydride. The obtained mixture was stirred at room temperature for several hours and distilled under a reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from ethyl acetate to give 0.64 g of the title compound as a pale yellow crystal.

Workup

  1. distillationdistilled under a reduced pressure
  2. customto remove the solvent
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-773caab339234b1d9fde1ccb798956fb
Source dataset
uspto-grants-2000_04
Patent number
US06046206

Reaction notes

Loading…