Methanol → HCID 18796797, compound

HRID 1938536Notes

Reaction equation

HRID 1938536 reaction equation
B(Cl)(Cl)Cl.C1[O:26][C:25]2[CH:24]=[CH:23][C:9]([CH2:10][NH:11][C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([Cl:22])[CH:20]=4)[N:15]=[CH:14][N:13]=3)=[CH:8][C:7]=2[O:6]1.CO>C(Cl)Cl.C(Cl)(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]([CH:23]=[CH:24][C:25]=1[OH:26])[CH2:10][NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([Cl:22])[CH:20]=2)[N:15]=[CH:14][N:13]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 25135Boron TrichlorideHCID 6610310N-(1,3-benzodioxol-5-ylmethyl)-6-chloroquinazolin-4-amine

Product 1

HCID 18796797HCID 18796797, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

40 ml of a 1.0 M solution of boron trichloride in methylene chloride was dropped into a solution of 2.00 g (6.37 mmol) of 4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline in 150 ml of chloroform under stirring at room temperature. The obtained mixture was stirred at room temperature for 2 days, followed by the addition of methanol, and the obtained mixture was distilled under a reduced pressure to remove the solvent. This procedure was repeated twice. The crystals thus precipitated were washed with methanol and recrystallized from ethanol to give 1.53 g of the title compound as a yellow crystal.

Workup

  1. stirringThe obtained mixture was stirred at room temperature for 2 days
  2. distillationthe obtained mixture was distilled under a reduced pressure
  3. customto remove the solvent
  4. customThe crystals thus precipitated
  5. washwere washed with methanol
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-b1cfb5333bb640a38e582e3167a40dcc
Source dataset
uspto-grants-1997_12
Patent number
US05693652

Reaction notes

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