Benzyl mercaptan → HCID 20376732, compound

HRID 596945Notes

Reaction equation

HRID 596945 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:8](Cl)=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[OH-].[K+].[CH2:14]([SH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([S:21][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 14797Potassium HydroxideHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 20376732HCID 20376732, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

86 g of 2-nitro-5-chloroaniline is dissolved in 400 ml of ethanol and the solution heated to 70° C internal temperature. An addition is made dropwise of a solution of 30.5 g of potassium hydroxide and 68 g of benzylmercaptan in 300 ml of ethanol. The reaction proceeds exothermically. Stirring is maintained overnight at the same internal temperature. The cooled mixture is stirred into ice water; the precipitate is filtered off under suction and recrystallised from ethanol to obtain 104.7 g (= 80% of theory) of 2-nitro-5-benzylthio-aniline, M.P. 113°-115° C.

Workup

  1. additionAn addition
  2. temperatureis maintained overnight at the same internal temperature
  3. filtrationthe precipitate is filtered off under suction
  4. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-65bef95afa084092b0b3faf1e67c30e4
Source dataset
uspto-grants-1977_03
Patent number
US04012512

Reaction notes

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