Ammonia → 6-methyl-5H-thiazolo-(2,3-b)-quinazolin-5-one

HRID 1086606Notes

Reaction equation

HRID 1086606 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH2:11])[C:7]=1[C:8]([NH2:10])=[O:9].Cl[C:13]1[S:14][CH:15]=[CH:16]N=1.N>O>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:7]=1[C:8](=[O:9])[N:10]1[CH:16]=[CH:15][S:14][C:13]1=[N:11]2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 764292-ChlorothiazoleHCID 167824692-Amino-6-methylbenzamide

Product 1

HCID 141004306-methyl-5H-thiazolo-(2,3-b)-quinazolin-5-oneYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

While stirring, 22.5 g of 6-methylanthranilamide was added to 18 g of 2-chlorothiazole. The reaction mixture was heated over a 20-minute period to 140° C. and stirred for 4 hours. Water was added to the reaction mixture, and a pH of 10 was set by adding 25% strength ammonia solution. Working up in the conventional manner gave 22.3 g (69%) of compound 3; m.p. 148°-150° C.

Workup

  1. stirringstirred for 4 hours

Sources & evidence

ORD record
ord-42b06d3991d9403ca7f102aecffac76c
Source dataset
uspto-grants-1991_07
Patent number
US05030727

Reaction notes

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