4-Chloro-3-nitrotoluene → 2-Chloro-5-methylaniline
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-])=O.S.[Na]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH2:9]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
514 Parts of 4-chloro-3-nitro-toluene and 300 parts of water were reacted in the same manner as described in Example 1 at from 90° to 95°C with 1446 parts of a 36% aqueous sodium hydrogen sulfide solution while stirring. Then, the 4-chloro-3-amino-toluene which had formed as by-product was eliminated by steam distillation. After cooling to 20° - 30°C, 1,210 parts of sodium sulfite (Na2SO3 . 7 H2O) and 430 parts of xylene were successively added and the pH was adjusted at 6 at a temperature within the range of from 10° to 12°C within from 2 to 3 hours with 565 parts of a 30% hydrochloric acid while stirring. For better separation of the phases, the mixture was heated at 25°C and the mother liquor was stirred with 174 parts of xylene. The 4-methyl-2-amino-thiophenol was isolated from the organic phase by vacuum distillation.
Sources & evidence
- ORD record
- ord-490ca37b22fa4468928d43dc27b9d035
- Source dataset
- uspto-grants-1976_01
- Patent number
- US03931321
Reaction notes
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