Thiophenol → HCID 13607938, compound

HRID 236080Notes

Reaction equation

HRID 236080 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2-].[Na+].Br[CH:11]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12]1>CS(C)=O.O>[CH2:16]([N:13]1[CH2:14][CH2:15][CH:11]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 24533Sodium amideHCID 151917211-Benzyl-3-bromopyrrolidine

Product 1

HCID 13607938HCID 13607938, compoundYield 727.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 55 g (0.5 mole) of thiophenol in 50 ml of dimethylsulfoxide was added dropwise with stirring to 250 ml of dimethylsulfoxide containing 21.5 g (0.55 mole) of sodamide. After stirring the mixture at 40° C. for 1 hr, 120 g (0.05 mole) of 3-bromo-1-benzyl-pyrrolidine (slightly exothermic) was added dropwise. The solution was stirred at 60° C. for 1 hr, diluted with 500 ml of water and extracted with isopropyl ether. The ether phase was dried over sodium sulfate and concentrated, and the residue distilled, b.p. 170°-170° C./5 mm. to give 98 g (73%) of product.

Workup

  1. stirringThe solution was stirred at 60° C. for 1 hr
  2. extractionextracted with isopropyl ether
  3. dry with materialThe ether phase was dried over sodium sulfate
  4. concentrationconcentrated
  5. distillationthe residue distilled

Sources & evidence

ORD record
ord-dd813d91cff14e57b7272496fdb2caa1
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Reaction notes

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