Dimethylformamide → HCID 13151850, compound

HRID 1074973Notes

Reaction equation

HRID 1074973 reaction equation
[C-]#N.[Na+].[Br:4][C:5]1[CH:6]=[C:7]([S:11][C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[CH2:14]Br)[CH:8]=[CH:9][CH:10]=1.[CH3:20][N:21](C)C=O>O>[Br:4][C:5]1[CH:6]=[C:7]([S:11][C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[CH2:14][C:20]#[N:21])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 13151849HCID 13151849, compound

Product 1

HCID 13151850HCID 13151850, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12.4 G. sodium cyanide (0.25 mole) is added to the solution of 58.6 g. 2-(3-bromophenylthio)benzyl bromide (0.164 mole) in 200 cc. dimethylformamide (DMF). The reaction is slightly exothermic. The resulting solution is allowed to stir for an hour without cooling, then is diluted with a large volume of water and extracted with ether three times. Ether extracts are washed several times with water, dried over sodium sulfate and the ether evaporated off. The crude yield of 2-(3-bromophenylthio)benzyl cyanide is 49.6 g.; the product is an oil which is hydrolyzed as such.

Workup

  1. temperaturewithout cooling
  2. extractionextracted with ether three times
  3. washEther extracts are washed several times with water
  4. dry with materialdried over sodium sulfate
  5. customthe ether evaporated off

Sources & evidence

ORD record
ord-747611d04b704d9c935e256a24cbb6e6
Source dataset
uspto-grants-1983_07
Patent number
US04394515

Reaction notes

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