Thiophenol → HCID 20161746, compound

HRID 247146Notes

Reaction equation

HRID 247146 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][C:9]([C:13]1[CH:18]=[CH:17][C:16](Br)=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1)([CH3:12])[C:10]#[N:11].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:8][C:9]([C:13]1[CH:18]=[CH:17][C:16]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1)([CH3:12])[C:10]#[N:11]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 10340Sodium CarbonateHCID 20161764Benzeneacetonitrile, 4-bromo-α,α-dimethyl-3-nitro-

Product 1

HCID 20161746HCID 20161746, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of thiophenol (9.09 g 0.0826 m), 2-methyl-2-(3-nitro-4-bromophenyl)propionitrile (18.68 g, 0.0694 m), sodium carbonate (16.0 g, 0.151 m) and absolute ethanol (300 ml) was stirred and heated at reflux for 5 hours. The cooled mixture was then poured onto ice-water and the resultant yellow solid filtered off. The crude solid was slurried with water/SVM (1.1, 300 ml) and the solid filtered and mixed with water/SVM (1:1, 150 ml. The solid was crystallised from methanol to give yellow needles (14.78 g, 65%) mpt. 146°-147° C. Calcd., for C16H14N2SO2 : C, 64.4 H, 4.7 N, 9.4; S, 10.7 Found: C, 64.5; H, 4.6; N, 9.3; S, 10.8

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. additionThe cooled mixture was then poured onto ice-water
  4. filtrationthe resultant yellow solid filtered off
  5. filtrationthe solid filtered
  6. additionmixed with water/SVM (1:1, 150 ml
  7. customThe solid was crystallised from methanol

Sources & evidence

ORD record
ord-1262a6b5b57b489cb49ee4adbfe2c3b4
Source dataset
uspto-grants-1987_11
Patent number
US04705854

Reaction notes

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