Sodium Hydroxide → 4,5-Dichloro-2-(4-oxo-3,4-dihydrothieno[3,2-d]pyrimidine-2-yl)benzoic acid

HRID 225462Notes

Reaction equation

HRID 225462 reaction equation
[OH-:1].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[Cl:13])[C:9](=O)[N:8]([C:15]1[CH:19]=[CH:18][S:17][C:16]=1[C:20]([NH2:22])=[O:21])[C:7]2=[O:23]>C1COCC1.CO>[Cl:13][C:12]1[C:4]([Cl:3])=[CH:5][C:6]([C:7]([OH:23])=[O:1])=[C:10]([C:9]2[NH:22][C:20](=[O:21])[C:16]3[S:17][CH:18]=[CH:19][C:15]=3[N:8]=2)[CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 690749393-(5,6-dichloro-1,3-dioxo-1,3-dihydro-2H-isoindole-2-yl)thiophene-2-carboxamide

Product 1

HCID 1363883024,5-Dichloro-2-(4-oxo-3,4-dihydrothieno[3,2-d]pyrimidine-2-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

3-aminothiophene-2-carboxamide was added to an acetic acid solution of 4,5-dichlorophthalic anhydride and stirred all night heated to reflux to give 3-(5,6-dichloro-1,3-dioxo-1,3-dihydro-2H-isoindole-2-yl)thiophene-2-carboxamide. 1M NaOH aq was added to THF-MeOH solution of the obtained 3-(5,6-dichloro-1,3-dioxo-1,3-dihydro-2H-isoindole-2-yl)thiophene-2-carboxamide and stirred for 2.5 hours at 80° C. to give 4,5-dichloro-2-(4-oxo-3,4-dihydrothieno[3,2-d]pyrimidine-2-yl)benzoic acid. Sulfuric acid was added to a MeOH-1,4-dioxane solution of the obtained 4,5-dichloro-2-(4-oxo-3,4-dihydrothieno[3,2-d]pyrimidine-2-yl)benzoic acid and stirred for three days at 70° C. to give methyl 4,5-dichloro-2-(4-oxo-3,4-dihydrothieno[3,2-d]pyrimidine-2-yl)benzoate.

Sources & evidence

ORD record
ord-3219a6d0f2c6418897a4a3f92c582c13
Source dataset
uspto-grants-2009_07
Patent number
US07557112B2

Reaction notes

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