Formic Acid → 3-(Formylamino)methylimidazo[5,1-b]thiazole
Reaction equation
[NH2:1][CH2:2][C:3]1[N:4]2[CH:10]=[N:9][CH:8]=[C:5]2[S:6][CH:7]=1.[CH:11](O)=[O:12].C(OC(=O)C)(=O)C.C(=O)([O-])O.[Na+]>ClCCl>[CH:11]([NH:1][CH2:2][C:3]1[N:4]2[CH:10]=[N:9][CH:8]=[C:5]2[S:6][CH:7]=1)=[O:12]Participants
Procedure
0.33 g of the above-obtained 3-aminomethylimidazo[5,1-b]-thiazole was dissolved in 10 ml of dichloromethane. To this solution, a mixture which had been prepared in advance by reacting 0.5 ml of formic acid with 0.5 ml of acetic anhydride at 50° C. for 10 minutes was added with stirring, and the resulting mixture was stirred at room temperature for an additional one hour. To the reaction solution was added 20 ml of a saturated aqueous solution of sodium hydrogencarbonate, and the organic layer was separated. The aqueous layer was extracted with dichloromethane (10 ml×2). The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated to dryness under reduced pressure to give 0.338 g (yield 87%) of the title compound.
Workup
- customTo this solution, a mixture which had been prepared in advance
- customat 50° C.
- customfor 10 minutes
- additionwas added
- stirringthe resulting mixture was stirred at room temperature for an additional one hour
- customthe organic layer was separated
- extractionThe aqueous layer was extracted with dichloromethane (10 ml×2)
- dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
- concentrationconcentrated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-f00eba499cae41e48c43b10f161cb31e
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05663162
Reaction notes
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