Sodium → HCID 13236222, compound

HRID 745219Notes

Reaction equation

HRID 745219 reaction equation
[Na].[OH:2][C:3]1(C2C=CC=CC=2)[NH:7][C:6](=[S:8])[C:5]([C:9]#[N:10])=[C:4]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)C>[C:11]1([C:4]2([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:3](=[O:2])[NH:7][C:6]([S:8][CH:4]([CH3:3])[CH2:5][CH3:6])=[C:5]2[C:9]#[N:10])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 132361755-Hydroxy-4,5-diphenyl-2-sulfanylidene-2,5-dihydro-1H-pyrrole-3-carbonitrile

Product 1

HCID 13236222HCID 13236222, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.8 g. Sodium is dissolved in 150 ml. absolute ethanol, 10.0 g. 5-hydroxy-4,5-diphenyl-2-thioxo-3-pyrroline-3-carbonitrile are added thereto and the reaction mixture is boiled for 30 minutes. The solvent is thereafter removed on a rotary evaporator and the residue is taken up in 100 ml. dimethylformamide. 5.1 g. sec.-Butyl bromide are added thereto, the reaction mixture is stirred for 24 hours at ambient temperature, a further 3.0 g. of the alkylating agent are again added thereto and stirring is continued for 24 hours. Thereafter, the solvent is distilled off under water pump vacuum and the residue is triturated with water. The precipitate is filtered off with suction, washed with water and crystallised from ethanol. There are obtained 7.0 g. of the desired product in the form of colourless crystals; m.p. 155°-156° C.

Workup

  1. customThe solvent is thereafter removed on a rotary evaporator
  2. additionsec.-Butyl bromide are added
  3. additionof the alkylating agent are again added
  4. stirringstirring
  5. waitis continued for 24 hours
  6. distillationThereafter, the solvent is distilled off under water pump vacuum
  7. customthe residue is triturated with water
  8. filtrationThe precipitate is filtered off with suction
  9. washwashed with water
  10. customcrystallised from ethanol
  11. customThere are obtained 7.0 g

Sources & evidence

ORD record
ord-2ae51dae6163461cb919b01d381b7807
Source dataset
uspto-grants-1986_07
Patent number
US04598076

Reaction notes

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