m-Anisoyl chloride → HCID 22732255, compound

HRID 1357678Notes

Reaction equation

HRID 1357678 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([Cl:8])=[O:7].[NH2:12][C:13]1[CH:14]=[C:15]([CH:31]=[CH:32][CH:33]=1)[NH:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1>C(Cl)Cl>[ClH:8].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:12][C:13]1[CH:14]=[C:15]([CH:31]=[CH:32][CH:33]=1)[NH:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1)=[O:7]

Participants

4

Reactant 2

HCID 74374m-Anisoyl chlorideHCID 11779327HCID 11779327, compound

Product 1

HCID 22732255HCID 22732255, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methoxybenzoyl chloride (0.169 ml) was added to a suspension of 4-(3-aminoanilino)-6,7-dimethoxyquinazoline (300 mg) in dry methylene chloride (10 ml). The reaction was stirred at ambient temperature for 18 hours. The precipitated solid was isolated, washed with methylene chloride and diethyl ether and then dried under vacuum to yield the title compound (398 mg, 85%); NMR: 3.84 (s, 3H), 3.98 (s, 3H), 4.02 (s, 3H), 7.15 (m, 1H), 7.35 (s, 1H), 7.4-7.56 (m, 5H), 7.66 (m, 1H), 8.21 (s, 1H), 8.31 (s, 1H), 8.8 (s, 1H), 10.41 (s, 1H), 11.38 (s, 1H); m/s: M+H+ 431.

Workup

  1. customThe precipitated solid was isolated
  2. washwashed with methylene chloride and diethyl ether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-819a4055fa9e488996d845c2d6be0153
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Reaction notes

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