Ammonia → HCID 21556754, compound

HRID 267298Notes

Reaction equation

HRID 267298 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[C:6](Br)=[CH:5][C:4]=1[CH:13]([CH3:15])[CH3:14].O.N.[CH3:18][N:19]1CCCC1=O>>[CH3:1][S:2][C:3]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[C:6]([C:18]#[N:19])=[CH:5][C:4]=1[CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 21556730HCID 21556730, compound

Product 1

HCID 21556754HCID 21556754, compound

Procedure

4-Cyano-2,5-diisopropylphenyl methyl sulfide was prepared as follows: A mixture of 20.4 g of 4-bromo-2,5-diisopropylphenyl methyl sulfide prepared as in Example 1C and 8.9 g of cuprous cyanide was heated at reflux in 100 ml of N-methylpyrrolidone under nitrogen for 2 hours. After cooling to ambient temperature, the reaction mixture was poured into a mixture of 200 ml of water and 100 ml of concentrated aqueous ammonia. The product was filtered and extracted into ether. The extract was washed with 5% HCl followed by a saturated solution of sodium chloride. The organic layer was dried over sodium sulfate and the solvent removed to give 15.5 g of 4-cyano-2,5-diisopropyl methyl sulfide which was recrystallized from n-hexane giving pure product having a melting point of 72°-75°C.

Workup

  1. temperaturewas heated
  2. filtrationThe product was filtered
  3. extractionextracted into ether
  4. washThe extract was washed with 5% HCl
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customthe solvent removed

Sources & evidence

ORD record
ord-95415ddfbde341748681f7dd269c937c
Source dataset
uspto-grants-1976_03
Patent number
US03941826

Reaction notes

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