p-Chlorothiophenol → HCID 20161751, compound

HRID 247147Notes

Reaction equation

HRID 247147 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[CH3:9][C:10]([C:14]1[CH:19]=[CH:18][C:17](Br)=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=1)([CH3:13])[C:11]#[N:12].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:13][C:10]([C:14]1[CH:19]=[CH:18][C:17]([S:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=1)([CH3:9])[C:11]#[N:12]

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 10340Sodium CarbonateHCID 20161764Benzeneacetonitrile, 4-bromo-α,α-dimethyl-3-nitro-

Product 1

HCID 20161751HCID 20161751, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-chlorothiophenol (6.5 g, 0.045 m), 2-methyl-2-(3-nitro-4-bromophenyl)propionitrile (11.0 g, 0.041 m), sodium carbonate (8.67 g, 0.082 m) and absolute ethanol (150 ml) as stirred and heated at reflux for 4 hours. The mixture was cooled and poured into ice-water and the resultant yellow solid was filtered off. This solid was then slurried in a mixture of water and SVM (1:1, 150 ml) and refiltered and washed with water/SVM (1:1, 150 ml). The solid was crystallised from ethanol to give yellow crystals (11.86 g, 87%) mpt. 159°-160°.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. temperatureThe mixture was cooled
  4. filtrationthe resultant yellow solid was filtered off
  5. additionThis solid was then slurried in a mixture of water and SVM (1:1, 150 ml)
  6. washwashed with water/SVM (1:1, 150 ml)
  7. customThe solid was crystallised from ethanol

Sources & evidence

ORD record
ord-eae3a60c0eaf40a8a8d25bc08f64b867
Source dataset
uspto-grants-1987_11
Patent number
US04705854

Reaction notes

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