Dimethylformamide → 2-Nitro-5-[(thiophen-3-yl)sulfanyl]aniline

HRID 1415533Notes

Reaction equation

HRID 1415533 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([SH:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CN(C)C=O.[H-].[Na+].Br[C:20]1[CH:24]=[CH:23][S:22][CH:21]=1>O>[NH2:1][C:2]1[CH:7]=[C:6]([S:8][C:20]2[CH:24]=[CH:23][S:22][CH:21]=2)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 133833-BromothiopheneHCID 24758Sodium hydrideHCID 213180223-Amino-4-nitrobenzene-1-thiol

Product 1

HCID 214827842-Nitro-5-[(thiophen-3-yl)sulfanyl]aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.4 G. of 2-amino-4-mercapto-1-nitrobenzene is dissolved in 40 ml. of dimethylformamide under nitrogen and treated at 20°-25° C with 0.5 g. of 100% sodium hydride. After 1 hour, 2.8 g. of cuprous oxide and 4.0 g. of 3-bromothiophene are added. The mixture is heated in an oil bath for 5 hours at 140°-150° C, cooled, diluted with water, and extracted with chloroform. The chloroform solution is passed through a silica gel column and the eluate evaporated to yield 2-amino-4-(3-thienylthio)-1-nitrobenzene.

Workup

  1. temperatureThe mixture is heated in an oil bath for 5 hours at 140°-150° C
  2. temperaturecooled
  3. extractionextracted with chloroform
  4. customthe eluate evaporated

Sources & evidence

ORD record
ord-074d7e20a3c44190bf10f00b5305fe8b
Source dataset
uspto-grants-1977_01
Patent number
US04005202

Reaction notes

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