Hydrazine hydrate (1:1) → 3-(tert-Butoxycarbonylamino)thiophene-2-carboxylic hydrazide

HRID 460313Notes

Reaction equation

HRID 460313 reaction equation
O.[NH2:2][NH2:3].[C:4]([O:8][C:9]([NH:11][C:12]1[CH:16]=[CH:15][S:14][C:13]=1[C:17]([O:19]C)=O)=[O:10])([CH3:7])([CH3:6])[CH3:5]>C(O)C>[C:4]([O:8][C:9]([NH:11][C:12]1[CH:16]=[CH:15][S:14][C:13]=1[C:17]([NH:2][NH2:3])=[O:19])=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18925408Methyl 3-((tert-butoxycarbonyl)amino)thiophene-2-carboxylate

Product 1

HCID 184459443-(tert-Butoxycarbonylamino)thiophene-2-carboxylic hydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.4 g of hydrazine hydrate is added to a solution of 1.3 g of methyl 3-(tert-butoxycarbonylamino)thiophene-2-carboxylate in 10 ml of ethanol and the mixture is heated to reflux for 5 hours. After the volatile fractions had been removed under reduced pressure at 40° C., the remaining oil was purified by column chromatography (silica gel, eluent: methylene chloride:methanol=95:5).

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 5 hours
  3. customAfter the volatile fractions had been removed under reduced pressure at 40° C.
  4. customthe remaining oil was purified by column chromatography (silica gel, eluent: methylene chloride:methanol=95:5)

Sources & evidence

ORD record
ord-03da844bef1c40678bacab9c4d44810d
Source dataset
uspto-grants-2007_03
Patent number
US07196114B2

Reaction notes

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