Ethylenediamine → HCID 21492141, compound

HRID 267301Notes

Reaction equation

HRID 267301 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[C:8](Br)=[CH:7][C:6]=1[CH:15]([CH3:17])[CH3:16])(=[O:4])=[O:3].C(N)[CH2:19][NH2:20]>CN1CCCC1=O.O>[CH3:1][S:2]([C:5]1[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[C:8]([C:19]#[N:20])=[CH:7][C:6]=1[CH:15]([CH3:17])[CH3:16])(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 21492094HCID 21492094, compound

Product 1

HCID 21492141HCID 21492141, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 4-bromo-2,5-diisopropylphenyl methyl sulfone (19.9 g) prepared in Example 10A and 7.2 g of cuprous cyanide was heated in 100 ml of N-methyl pyrrolidone at 195°C under nitrogen for 2 hours. The reaction mixture was poured into a stirred solution of 25 g of ethylenediamine in 500 ml of water. The mixture was filtered and the residual product extracted into tetrahydrofuran. The extract was washed with 5% HCl and finally with saturated sodium chloride solution. After drying over magnesium sulfate, the solvent was removed to give 4-cyano-2,5-diisopropylphenyl methyl sulfone. Further purification by recrystallization from n-hexane gave 4-cyano-2,5-diisopropylphenyl methyl sulfone having a mp of 134°-137°C.

Workup

  1. filtrationThe mixture was filtered
  2. extractionthe residual product extracted into tetrahydrofuran
  3. washThe extract was washed with 5% HCl and finally with saturated sodium chloride solution
  4. dry with materialAfter drying over magnesium sulfate
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-c3fa08a11d194d328fd7ea526d095f85
Source dataset
uspto-grants-1976_03
Patent number
US03941826

Reaction notes

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