Ammonia → HCID 19005541, compound

HRID 1742783Notes

Reaction equation

HRID 1742783 reaction equation
[CH2:1]([CH:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)=[CH:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].N.[CH3:20][N:21](C)C=O>>[CH2:1]([CH:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:20]#[N:21])=[CH:14][CH:13]=2)=[CH:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 19005609HCID 19005609, compound

Product 1

HCID 19005541HCID 19005541, compound

Procedure

In 15 ml of N,N-dimethylformamide, 4 g of the 1-pentyl-4-(4-bromophenyl)dihydrobenzene, which had been obtained in Example 8, were dissolved, followed by the addition of 1.4 g of cuprous cyanide. The resulting mixture was reacted for 6 hours at reflux temperature. After the completion of the reaction, aqueous ammonia was added to the reaction mixture, followed by the extraction of the reaction mixture with toluene. The extract was washed with aqueous ammonia and then with saturated NaCl. Anhydrous sodium sulfate was thereafter added to dry the extract. The toluene was distilled off under reduced pressure. The reaction product so obtained was recrystallized twice from ethanol, whereby 0.8 g of 1-pentyl-4-(4-cyanophenyl)dihydrobenzene was obtained.

Workup

  1. dissolutionwere dissolved
  2. customThe resulting mixture was reacted for 6 hours
  3. temperatureat reflux temperature
  4. additionwas added to the reaction mixture
  5. extractionfollowed by the extraction of the reaction mixture with toluene
  6. washThe extract was washed with aqueous ammonia
  7. additionAnhydrous sodium sulfate was thereafter added
  8. customto dry the extract
  9. distillationThe toluene was distilled off under reduced pressure
  10. customThe reaction product so obtained
  11. customwas recrystallized twice from ethanol

Sources & evidence

ORD record
ord-fc6c93a1e91541a48091dd45b779564c
Source dataset
uspto-grants-1994_08
Patent number
US05342546

Reaction notes

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