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Dimethyl Sulfoxide → 2-Cyano-2-(4-phenylthiophenyl)hexyl bromide

HRID 128225
Notes
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Reaction equation

HRID 128225 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH2:17][CH2:18][CH2:19][CH3:20])[C:15]#[N:16])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:21][CH2:22]Br.CS(C)=O.[OH-].[Na+]>O>[C:15]([C:14]([C:11]1[CH:12]=[CH:13][C:8]([S:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:9][CH:10]=1)([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:22][Br:21])#[N:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 3024DibromomethaneHCID 14798Sodium HydroxideHCID 544229802-(4-Phenylthiophenyl) hexanenitrile

Product 1

HCID 542149592-Cyano-2-(4-phenylthiophenyl)hexyl bromideYield 101.5%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

To a mixture of 31 g (0.1 mole) of 2-(4-phenylthiophenyl) hexanenitrile, 22 g (0.13 mole) of dibromomethane and 100 ml of dimethyl sulfoxide is added 12 g (0.15 mole) of 50% sodium hydroxide solution dropwise with stirring. Reaction mixture is stirred at 60° for 1/2 hour and then poured into water and extracted with ether. The combined ether extracts are washed with water and dried over MgSO4. Solvent is evaporated to give 38 g of product.

Workup

  1. customReaction mixture
  2. stirringis stirred at 60° for 1/2 hour
  3. extractionextracted with ether
  4. washThe combined ether extracts are washed with water
  5. dry with materialdried over MgSO4
  6. customSolvent is evaporated

Sources & evidence

ORD record
ord-ddc8e370cf324180bfbb1c36176028c5
Source dataset
uspto-grants-1981_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04259339

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes