Sulfuric Acid → Methyl 4,5-dichloro-2-(4-oxo-3,4-dihydrothieno[3,2-d]pyrimidine-2-yl)benzoate
Reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[C:15]([Cl:16])=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([C:17]2[NH:18][C:19](=[O:26])[C:20]3[S:25][CH:24]=[CH:23][C:21]=3[N:22]=2)[CH:8]=1.CO.O1CCOC[CH2:30]1>>[Cl:6][C:7]1[C:15]([Cl:16])=[CH:14][C:10]([C:11]([O:13][CH3:30])=[O:12])=[C:9]([C:17]2[NH:18][C:19](=[O:26])[C:20]3[S:25][CH:24]=[CH:23][C:21]=3[N:22]=2)[CH:8]=1Participants
Conditions
- Temperature
- 70 °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-64165a14352946459621c2e2394358d0
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557112B2
Reaction notes
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