Sodium Hydroxide → HCID 9904156, compound

HRID 582003Notes

Reaction equation

HRID 582003 reaction equation
Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].[OH-:8].[Na+].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](C)=[C:18]([C:22]#[N:23])[C:19]([NH2:21])=S)=[CH:13][CH:12]=1>C(O)C>[NH2:23][C:22]1[N:6]([C:2]([CH3:5])([CH3:4])[CH3:3])[N:7]=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][CH:13]=2)[C:18]=1[C:19]([NH2:21])=[O:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 81889tert-Butylhydrazine monohydrochlorideHCID 57075473HCID 57075473, compound

Product 1

HCID 9904156HCID 9904156, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl hydrazine hydrochloride (523 mg, 3.50 mmol) in ethyl alcohol (20 ml) was added powdered sodium hydroxide (168 mg, 4.20 mmol), followed by 3-(4-chlorophenyl)-2-cyano-3-methylthioacrylamide (884 mg, 3.50 mmol) and the mixture was heated at reflux for 4 h. On cooling, the solvent was removed under reduced pressure and the residue partitioned between water (80 ml) and ethyl acetate (80 ml). The aqueous layer was further extracted with ethyl acetate (2×80 ml) and the combined organic layers were washed with brine (1×100 ml), dried (MgSO4) and concentrated under reduced pressure. The residue was subjected to column chromatography (SiO2, 45-75% ethyl acetate-hexane) to afford the title compound (780 mg) after recrystallisation from methanol as a colorless solid m.p. 156°. δH (d6DMSO) 1.66 (9H, s), 5.16 (2H, br s), 5.68 (2H, br s), 7.42 (2H, dt, J 8.6, 2.1 Hz), and 7.51 (2H, dt, J 8.7, 2.1 Hz).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 h
  3. temperatureOn cooling
  4. customthe solvent was removed under reduced pressure
  5. customthe residue partitioned between water (80 ml) and ethyl acetate (80 ml)
  6. extractionThe aqueous layer was further extracted with ethyl acetate (2×80 ml)
  7. washthe combined organic layers were washed with brine (1×100 ml)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d6c37688e6cd4da885a156c804a3c668
Source dataset
uspto-grants-1999_07
Patent number
US05922741

Reaction notes

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