Triethylamine → 2-(4-Chlorobenzoylamino)-4,5-dimethoxybenzamide

HRID 2408947Notes

Reaction equation

HRID 2408947 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1.C(N(CC)CC)C>C1COCC1>[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH:1][C:2]2[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=2[C:4]([NH2:6])=[O:5])=[O:21])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 108672362-Amino-4,5-dimethoxybenzamide

Product 1

HCID 229974052-(4-Chlorobenzoylamino)-4,5-dimethoxybenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As shown in scheme Q, 2-amino-4,5-dimethoxybenzamide is reacted with 4-chlorobenzoyl chloride in presence of triethyl amine and THF to give 2-((4-chlorophenyl)carbonylamino)-4,5-dimethoxybenzamide. Which is cyclised using NaOH and then treated with thionyl chloride to give 4-chloro-2-(4-chlorophenyl)-6,7-dimethoxyquinazoline (McKee, R. L. et. al., J. Am. Chem. Soc., 1946, 68, 1902-1903). The 4-chlorocompound is treated with 5-(tert-butyl)selenophene-2-carboxamide in the presence of NaOH/DMF to give 3-(2-(4-chlorophenyl)-6,7-dimethoxyquinazolin-4-ylamino)-5-tert-butylselenophene-2-carboxamide.

Sources & evidence

ORD record
ord-7e9afdc42e0b4a639d5b0bd5c9bb03a6
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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