2,5-Dichloronitrobenzene → 2,5-Dichloroaniline
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-])=O.S.[Na]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH2:9]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
384 Parts of 2,5-dichloronitrobenzene and 200 parts of water were introduced into a stirring apparatus and reacted with 1,000 parts of 36% sodium hydrogensulfide solution in the same manner as described in Example 1. Then, the 2,5-dichloroaniline obtained as by-product was separated by steam distillation. After cooling to 20°C 806 parts of sodium sulfite (Na2SO3 . 7 H2O) were added and the pH was adjusted at 6 with 374 parts of 30% hydrochloric acid at a temperature within the range of from +10°C to 12°C within 2 to 3 hours while stirring. The precipitated solid reaction product was suction-filtered, dissolved in 1,000 parts of a 8% sodium hydroxide solution at 50° to 60°C to separate the sulfur and the disulfide; the solution was suction-filtered from the undissolved moiety and 4-chloro-2-aminothiophenol was precipitated from the filtrate at room temperature (20° C) with 242 parts of 30% hydrochloric acid.
Sources & evidence
- ORD record
- ord-82f969fb8b7f45d4851dcbae80517dc4
- Source dataset
- uspto-grants-1976_01
- Patent number
- US03931321
Reaction notes
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