Hydrazine → HCID 13451341, compound

HRID 2379462Notes

Reaction equation

HRID 2379462 reaction equation
[IH:1].[C:2]1([NH:8][C:9](SC)=[NH:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:13][NH2:14]>C(O)C>[IH:1].[C:2]1([N:8]=[C:9]([NH:13][NH2:14])[NH2:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 178503974HCID 178503974, compound

Product 1

HCID 13451341HCID 13451341, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred room temperature suspension of phenyl-carbamimidothioic acid, methyl ester, monohydroiodide (91.5 g, 0.311 mol) in absolute ethanol (280 mL) was added in one portion anhydrous hydrazine (9.8 mL, 0.31 mol), and the mixture was heated to reflux. The mixture was refluxed for 3 hours and allowed to cool. The resulting solution was purged with nitrogen to remove methanethiol and rotary evaporated to an oil. The oil was dried in vacuo briefly then dissolved in water (130 mL). The solution was rotoevaporated to an oil. The oil was dried in vacuo (50° C.), yield 87.08 g (100%). 1H NMR (DMSO-d6): δ 9.5 (br s, 0.5H), 9.0 (br s, 1.5H), 7.7 (br s, 2H), 7.4 (t, 2H), 7.2 (m, 3H), 4.8 (br s, 2H).

Workup

  1. temperaturethe mixture was heated to reflux
  2. temperatureThe mixture was refluxed for 3 hours
  3. temperatureto cool
  4. customThe resulting solution was purged with nitrogen
  5. customto remove methanethiol
  6. customrotary evaporated to an oil
  7. customThe oil was dried in vacuo briefly
  8. dissolutiondissolved in water (130 mL)
  9. customThe oil was dried in vacuo (50° C.), yield 87.08 g (100%)

Sources & evidence

ORD record
ord-c0e17bbe281d4c488c42a3c359a22839
Source dataset
uspto-grants-1994_11
Patent number
US05362744

Reaction notes

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