Sodium Hydroxide → HCID 15541842, compound

HRID 1699772Notes

Reaction equation

HRID 1699772 reaction equation
O.[NH2:2][NH2:3].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([S:26][CH3:27])=[CH:22][CH:21]=2)=O)[CH2:12][C:13](OCC)=[O:14])=[CH:7][CH:6]=1.[OH-].[Na+]>C(O)C>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:18]([C:20]3[CH:25]=[CH:24][C:23]([S:26][CH3:27])=[CH:22][CH:21]=3)=[N:3][NH:2][C:13](=[O:14])[CH2:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 15541841HCID 15541841, compound

Product 1

HCID 15541842HCID 15541842, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Hydrazine hydrate (10.56 g, 210.9 mmol) was added to a solution of ethyl 3-(4-chlorophenyl)-4-[4-(methylthio)phenyl]-4-oxobutanoate (42.54 g, 117.2 mmol) in ethanol (85 ml), followed by heating under reflux for 15 hours at a bath temperature of 100° C. A 4 N aqueous solution of sodium hydroxide (40 ml) was added to the reaction mixture. After the mixture was ice-cooled, precipitated crystals were collected by filtration, washed with water (3×100 ml), dried in air, and then dried under reduced pressure (100° C., 2 hours), whereby the title compound (31.49 g, 81.2%) was obtained as pale yellow crystalline powder.

Workup

  1. temperatureby heating
  2. temperaturecooled
  3. customprecipitated crystals
  4. filtrationwere collected by filtration
  5. washwashed with water (3×100 ml)
  6. customdried in air
  7. dry with materialdried under reduced pressure (100° C., 2 hours), whereby the title compound (31.49 g, 81.2%)
  8. customwas obtained as pale yellow crystalline powder

Sources & evidence

ORD record
ord-07cb58974e8f4e278c675bc4689b2b95
Source dataset
uspto-grants-2002_02
Patent number
US06348468B1

Reaction notes

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