Thiophenol → 5-Nitro-2-(phenylsulfanyl)benzaldehyde

HRID 435615Notes

Reaction equation

HRID 435615 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5].[C:13]1([SH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C.[OH-].[Na+].O>[N+:10]([C:7]1[CH:6]=[C:3]([C:2]([S:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[CH:4]=[O:5])([O-:12])=[O:11]

Participants

6

Reactant 2

HCID 7969ThiophenolHCID 729332-Chloro-5-nitrobenzaldehyde

Product 1

HCID 29810675-Nitro-2-(phenylsulfanyl)benzaldehyde

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 480 g of 2-chloro-5-nitro-benzaldehyde in 3.2 litres of ethanol is treated dropwise under a nitrogen atmosphere at 30°-40° C with stirring within 4 hours with a solution of 320 g of thiophenol in 120 g of sodium hydroxide, 2 litres of ethanol and 440 ml of water. The mixture is stirred for a further 30 minutes at 60° C, then cooled to 0° C and filtered. There is obtained crude crystalline 3-nitro-6-(phenylthio)-benzaldehyde of melting point 96°-100° C.

Workup

  1. temperaturecooled to 0° C
  2. filtrationfiltered

Sources & evidence

ORD record
ord-ec4073e462494ac3a397f1e72403e69a
Source dataset
uspto-grants-1977_02
Patent number
US04006145

Reaction notes

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