Hydrazine hydrate (1:1) → 2-Amino-4-cyclopropyl-1,3-thiazole-5-carbohydrazide
Reaction equation
Br.[NH2:2][C:3]1[S:4][C:5]([C:11]([O:13]C)=O)=[C:6]([CH:8]2[CH2:10][CH2:9]2)[N:7]=1.O.[NH2:16][NH2:17]>CO>[NH2:2][C:3]1[S:4][C:5]([C:11]([NH:16][NH2:17])=[O:13])=[C:6]([CH:8]2[CH2:10][CH2:9]2)[N:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
Methyl 2-amino-4-cyclopropyl-1,3-thiazole-5-carboxylate hydrobromide (1.78 g) was dissolved in methanol (4.0 ml), hydrazine monohydrate (2.0 ml) was added thereto, followed by stirring at 55° C. for 3 days. After cooling to room temperature, an insoluble substance was filtered, the mother solution was mixed with basic silica gel and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel chromatography (chloroform:methanol) to obtain, as a dark brown solid, 2-amino-4-cyclopropyl-1,3-thiazole-5-carbohydrazide (224 mg).
Workup
- temperatureAfter cooling to room temperature
- filtrationan insoluble substance was filtered
- additionthe mother solution was mixed with basic silica gel
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by basic silica gel chromatography (chloroform:methanol)
Sources & evidence
- ORD record
- ord-309afcba4bca442eb3f07c12bba5c19f
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08377923B2
Reaction notes
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