Hydrazine → HCID 68137094, compound

HRID 1576026Notes

Reaction equation

HRID 1576026 reaction equation
[C:1]1([CH:7]=[C:8]2[C:13](=O)[C:12](=[CH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][S:10](=[O:23])(=[O:22])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:24][NH2:25]>CO>[C:1]1([CH:7]2[NH:25][N:24]=[C:13]3[C:12](=[CH:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:11][S:10](=[O:23])(=[O:22])[CH2:9][CH:8]23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 53941400HCID 53941400, compound

Product 1

HCID 68137094HCID 68137094, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5.0g of tetrahydro-3,5-bis-(phenylmethylene)-4H-thiopyran-4-one-1,1-dioxide and 600mg of anhydrous hydrazine in 300ml of methanol is heated at reflux temperature for 2 hours. The mixture is cooled in an ice bath, filtered, and the product is washed with fresh methanol. The filtrate and washings are concentrated to about 100ml and cooled in an ice bath, yielding an additional small amount of product. The combined yield is 4.7g of the title compound, melting point 202°-208°C, dec.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 2 hours
  3. temperatureThe mixture is cooled in an ice bath
  4. filtrationfiltered
  5. washthe product is washed with fresh methanol
  6. concentrationThe filtrate and washings are concentrated to about 100ml
  7. temperaturecooled in an ice bath
  8. customyielding an additional small amount of product

Sources & evidence

ORD record
ord-ee4fc5d0ad514b44b731f996c3960be6
Source dataset
uspto-grants-1976_09
Patent number
US03979381

Reaction notes

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