Hydrazine hydrate (1:1) → Tert-butyl 4-cyano-5-hydrazinothiophene-2-carboxylate

HRID 1096152Notes

Reaction equation

HRID 1096152 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[S:6][C:7]=1S(C)(=O)=O)#[N:2].O.[NH2:20][NH2:21]>CO.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[S:6][C:7]=1[NH:20][NH2:21])#[N:2]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66785761Tert-butyl 4-cyano-5-(methylsulfonyl)thiophene-2-carboxylate

Product 1

HCID 11622817Tert-butyl 4-cyano-5-hydrazinothiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of tert-butyl 4-cyano-5-(methylsulfonyl)thiophene-2-carboxylate (2.0 g, 7.0 mmol) and hydrazine hydrate (1.7 mL) in methyl alcohol (30 mL) was stirred at 60° C. for 2 hours. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with water. Organic layer was separated, dried over anhydrous sodium sulfate and evaporated. Through chromatography purification (n-hexane/ethyl acetate 3:2), 1 g of the title compound was thus obtained.

Workup

  1. washwashed with water
  2. customOrganic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThrough chromatography purification (n-hexane/ethyl acetate 3:2), 1 g of the title compound
  6. customwas thus obtained

Sources & evidence

ORD record
ord-d1c8815be73c441b93a2ef2e2ef60399
Source dataset
uspto-grants-2012_03
Patent number
US08138217B2

Reaction notes

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