Methylhydrazine → HCID 22054401, compound

HRID 1835139Notes

Reaction equation

HRID 1835139 reaction equation
[CH3:1][CH:2]([CH3:14])[CH2:3][C:4]([C:6]1[S:7][CH:8]=[CH:9][C:10]=1[C:11](O)=[O:12])=O.[CH3:15][NH:16][NH2:17]>C(O)C.C(OCC)(=O)C>[CH3:15][N:16]1[C:11](=[O:12])[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[C:4]([CH2:3][CH:2]([CH3:14])[CH3:1])=[N:17]1

Participants

5

Reactant 2

HCID 6061MethylhydrazineHCID 23503279HCID 23503279, compound

Product 1

HCID 22054401HCID 22054401, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(3-Methyl-1-oxobutyl)thiophene-3-carboxylic acid (5.3 g) prepared in a) above was dissolved in ethanol (30 ml) and methylhydrazine (1.5 ml) added. The resultant mixture was heated to reflux for 10 hours. The reaction mixture was evaporated and the residue obtained was dissolved in ethyl acetate. The organic phase was washed twice with dilute hydrochloric acid, twice with saturated sodium hydrogen carbonate solution and once with brine, then dried and evaporated. Purification by chromatography eluting with iso-hexane/ethyl acetate (2:1 to 1:1) gave the sub-title compound as an oil (3.05 g).

Workup

  1. temperatureto reflux for 10 hours
  2. customThe reaction mixture was evaporated
  3. customthe residue obtained
  4. washThe organic phase was washed twice with dilute hydrochloric acid, twice with saturated sodium hydrogen carbonate solution and once with brine
  5. customdried
  6. customevaporated
  7. customPurification by chromatography
  8. washeluting with iso-hexane/ethyl acetate (2:1 to 1:1)

Sources & evidence

ORD record
ord-e3c19add958746a0a68e15fe40a0610b
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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