Hydrazine, propyl- → HCID 54469210, compound

HRID 1576018Notes

Reaction equation

HRID 1576018 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.[CH2:24]([NH:27][NH2:28])[CH2:25][CH3:26]>CO.C(Cl)(Cl)(Cl)Cl>[C:1]1([CH:7]2[N:27]([CH2:24][CH2:25][CH3:26])[N:28]=[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

5

Reactant 2

HCID 42007Hydrazine, propyl-HCID 53941400HCID 53941400, compound

Product 1

HCID 54469210HCID 54469210, compoundYield 48.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3.24g of tetrahydro-3,5-bis-(phenylmethylene)-4H-thiopyran-4-one-1,1-dioxide and 0.6g of n-propyl hydrazine in 100ml of absolute methanol is heated at reflux temperature for 2 hours. The mixture is allowed to cool, and is then filtered to give 2.8g of crude product. The crude material is stirred for about 16 hours in 200ml of carbon tetrachloride and filtered. The mother liquor is concentrated in vacuo and the residue is crystallized from methanol to give 1.5g of the title compound, melting point 197°-199°C.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 2 hours
  3. temperatureto cool
  4. filtrationis then filtered
  5. customto give 2.8g of crude product
  6. filtrationfiltered
  7. concentrationThe mother liquor is concentrated in vacuo
  8. customthe residue is crystallized from methanol

Sources & evidence

ORD record
ord-5d8b07a025154074903a2bb6640a1e27
Source dataset
uspto-grants-1976_09
Patent number
US03979381

Reaction notes

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