Hydrochloric Acid → 2-(4-Chlorophenyl)-4-(2-thienyl)butyronitrile

HRID 2255386Notes

Reaction equation

HRID 2255386 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][C:9]#[N:10])=[CH:6][CH:5]=1.CS(O[CH2:18][CH2:19][C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)(=O)=O.Cl>CCCCCC.CN(C=O)C>[Cl:3][C:4]1[CH:12]=[CH:11][C:7]([CH:8]([CH2:18][CH2:19][C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)[C:9]#[N:10])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2415824-Chlorobenzyl cyanideHCID 30477232-(2-Thienyl)ethyl methanesulphonate

Product 1

HCID 197380262-(4-Chlorophenyl)-4-(2-thienyl)butyronitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
10 °C

Procedure

To a flask under a nitrogen atmosphere was added, with stirring, 3.3 g. (0.0825 mole) of 60% sodium hydride, washed twice with hexane to remove the original mineral oil, in 75 ml. of a dry 2 to 1 mixture of DMF and toluene. To this slurry at room temperature was added 11.30 g. (0.075 mole) of 4-chlorobenzyl cyanide in 40 ml. of DMF. After 1.5 hours, the mixture was cooled to 10° C. and 13.7 g. (0.0782 mole) of 2-(2-thienyl)ethyl methanesulfonate in 25 ml. of DMF was added dropwise. The reaction was stirred at room temperature for 13 hours. Then aqueous 10% hydrochloric acid, 20 ml., was added followed by 150 ml. of diethyl ether which was washed three times with 50 ml. portions of water. After drying the ether and concentrating, the product was distilled at 130°-150° C. at 1-2 mm of Hg yielding 2-(4-chlorophenyl)-4-(2-thienyl)butyronitrile as an oil.

Workup

  1. additionTo a flask under a nitrogen atmosphere was added
  2. customto remove the original mineral oil
  3. customof a dry 2
  4. additionto 1 mixture of DMF and toluene
  5. additionTo this slurry at room temperature was added 11.30 g
  6. stirringThe reaction was stirred at room temperature for 13 hours
  7. addition, was added
  8. washof diethyl ether which was washed three times with 50 ml
  9. dry with materialAfter drying the ether
  10. concentrationconcentrating
  11. distillationthe product was distilled at 130°-150° C. at 1-2 mm of Hg

Sources & evidence

ORD record
ord-8680e3bb56fb4e5eb8177477264c4bf5
Source dataset
uspto-grants-1993_08
Patent number
US05240925

Reaction notes

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