Sodium benzenethiolate → 2-Chloro-3-phenylthio-6-nitro-N-methylaniline

HRID 1074848

Reaction equation

HRID 1074848 reaction equation
[C:1]1([S-:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].[Cl:9][C:10]1[C:17](Cl)=[CH:16][CH:15]=[C:14]([N+:19]([O-:21])=[O:20])[C:11]=1[NH:12][CH3:13]>C(#N)C>[Cl:9][C:10]1[C:17]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:16][CH:15]=[C:14]([N+:19]([O-:21])=[O:20])[C:11]=1[NH:12][CH3:13]

Participants

4

Reactant 2

HCID 4110039Sodium benzenethiolateHCID 204396362,3-dichloro-N-methyl-6-nitroaniline

Product 1

HCID 204950262-Chloro-3-phenylthio-6-nitro-N-methylaniline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

An amount of 2.9 gm of sodium thiophenolate was added to a solution of 4.4 gm (0.02 mol) of 2,3-dichloro-6-nitro-N-methylaniline dissolved in 50 ml of acetonitrile. The mixture was refluxed for half an hour and subsequently evaporated, and the residue was taken up with chloroform and water. The chloroform layer was separated, dried, and evaporated. Six grams of brown oil, which crystallized with isopropanol, were obtained. The yield from the crystallization was 4 gm of product (67.5% of theory) in the form of yellow crystals, m.p. 79° C.

Workup

  1. temperatureThe mixture was refluxed for half an hour
  2. customsubsequently evaporated
  3. customThe chloroform layer was separated
  4. customdried
  5. customevaporated
  6. customSix grams of brown oil, which crystallized with isopropanol
  7. customwere obtained
  8. customThe yield from the crystallization

Sources & evidence

ORD record
ord-f2d4cd2ada3d4c7b835e61681b1ae5d2
Source dataset
uspto-grants-1983_07
Patent number
US04394159

Linked notes

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