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Hydrazine hydrate (1:1) → 2-Amino-4-cyclopropyl-1,3-thiazole-5-carbohydrazide

HRID 389099
Notes
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Reaction equation

HRID 389099 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]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86653012Methyl 2-amino-4-cyclopropyl-1,3-thiazole-5-carboxylate hydrobromide

Product 1

HCID 582439332-Amino-4-cyclopropyl-1,3-thiazole-5-carbohydrazide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. temperatureAfter cooling to room temperature
  2. filtrationan insoluble substance was filtered
  3. additionthe mother solution was mixed with basic silica gel
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by basic silica gel chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-309afcba4bca442eb3f07c12bba5c19f
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08377923B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes