2-Bromopropane → HCID 13236221, compound

HRID 745218Notes

Reaction equation

HRID 745218 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.[CH:23](Br)([CH3:25])[CH3:24]>C(O)C>[C:23]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:11]([CH3:16])[CH3:12])=[C:5]2[C:9]#[N:10])[CH:25]=[CH:5][CH:4]=[CH:3][CH:24]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 5360545SodiumHCID 132361755-Hydroxy-4,5-diphenyl-2-sulfanylidene-2,5-dihydro-1H-pyrrole-3-carbonitrile

Product 1

HCID 13236221HCID 13236221, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.2 g. Sodium is dissolved in 150 ml. ethanol, 15.2 g. 5-hydroxy-4,5-diphenyl-2-thioxo-3-pyrroline-3-carbonitrile are added thereto and the reaction mixture is then boiled for 20 minutes. A solution of 7.0 g. isopropyl bromide in 25 ml. absolute ethanol is then added dropwise thereto within the course of 10 minutes and refluxing continued for a further 3 hours. After cooling, the solvent is stripped off on a rotary evaporator and the residue is triturated with 100 ml. water. The precipitate is filtered off with suction and crystallised from ethanol. There are obtained 11.1 g. (64.0% of theory) of the desired product in the form of colourless crystals; m.p. 160° C.

Workup

  1. temperaturewithin the course of 10 minutes and refluxing
  2. waitcontinued for a further 3 hours
  3. temperatureAfter cooling
  4. customthe solvent is stripped off on a rotary evaporator
  5. customthe residue is triturated with 100 ml
  6. filtrationThe precipitate is filtered off with suction
  7. customcrystallised from ethanol
  8. customThere are obtained 11.1 g

Sources & evidence

ORD record
ord-3ee933ee1c684ca58f1ddcf72e715ed3
Source dataset
uspto-grants-1986_07
Patent number
US04598076

Reaction notes

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