Hydrazine hydrate (1:1) → HCID 178482959, compound

HRID 415434Notes

Reaction equation

HRID 415434 reaction equation
[CH3:1][N:2]([CH3:9])[C:3](SC)=[CH:4][C:5]#[N:6].O.[NH2:11][NH2:12]>C(O)C>[CH3:1][N:2]([CH3:9])[C:3]1[NH:12][N:11]=[C:5]([NH2:6])[CH:4]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68605084HCID 68605084, compound

Product 1

HCID 178482959HCID 178482959, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of (2E or Z)-3-(dimethylamino)-3-(methylthio)acrylonitrile (Method 33, 9.525 g, 67 mmol) and hydrazine hydrate (10.06 g, 201 mmol) in ethanol (70 ml) was heated at 85° C. overnight. Solvent was removed. The residue was purified by silica gel column chromatography (by ISCO Combiflash with a gradient of 0-10% methanol in methylenechloride with 1% NH4OH). 5.8 g (69%) product as obtained brownish thick oil. LC-MS, 127 (M+1). NMR (DMSO, 400 MHz) δ9.51 (br, 1H), 4.67 (s, 1H), 2.62 (s, 6H).

Workup

  1. customSolvent was removed
  2. customThe residue was purified by silica gel column chromatography (by ISCO Combiflash with a gradient of 0-10% methanol in methylenechloride with 1% NH4OH)

Sources & evidence

ORD record
ord-f6f5696b49414942ab4de9fc2ec7bef4
Source dataset
uspto-grants-2012_01
Patent number
US08088784B2

Reaction notes

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