HCID 10799101, compound → HCID 18184425, compound

HRID 1358261Notes

Reaction equation

HRID 1358261 reaction equation
[N+:1]([C:4]1[C:5]([C:13]([NH2:15])=[O:14])=[CH:6][C:7]2[S:11][CH:10]=[N:9][C:8]=2[CH:12]=1)([O-])=O>CO.CCOC(C)=O.[Pd]>[NH2:1][C:4]1[C:5]([C:13]([NH2:15])=[O:14])=[CH:6][C:7]2[S:11][CH:10]=[N:9][C:8]=2[CH:12]=1

Participants

4

Reactant 1

HCID 10799101HCID 10799101, compound

Product 1

HCID 18184425HCID 18184425, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of 5-nitrobenzothiazole-6-carboxamide (0.30 g, 1.34 mmol) in MeOH/EtOAc (1:1, 25 mL) is hydrogenated over 5% Pd/C at 60 psi for 1 h to give 5-aminobenzothiazole-6-carboxamide. This is immediately dissolved in triethyl orthoformate (30 mL) and the mixture is heated under gentle reflux for 18 h. An equal volume of petroleum ether is added to the cooled solution, precipitating thiazolo[5,4-g]quinazol-4(3H)-one (0.17 g, 57%) as a tan powder. 1H NMR (DMSO) δ12.30 (1H, brs), 9.67 (1H, s). 9.00 (1H, s), 8.31 (1H, s), 8.14 (1H, s).

Sources & evidence

ORD record
ord-14e8843224b7468d80dbb444282b2451
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

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