4-Bromothiophenol → HCID 22621246, compound

HRID 841193Notes

Reaction equation

HRID 841193 reaction equation
[Na].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.Cl[C:11]1[CH:12]=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[C:15]([CH:17]=1)[NH2:16]>C(O)C>[NH2:16][C:15]1[CH:17]=[C:11]([S:9][C:6]2[CH:7]=[CH:8][C:3]([Br:2])=[CH:4][CH:5]=2)[CH:12]=[CH:13][C:14]=1[N+:18]([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 660494-BromothiophenolHCID 742185-Chloro-2-nitroanilineHCID 5360545Sodium

Product 1

HCID 22621246HCID 22621246, compoundYield 6,262.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (0.269 g) was added to ethanol (20 ml) and the resultant solution was allowed to cool to ambient temperature then 4-bromothiophenol (2.21 g) was added. The mixture was stirred for 5 minutes then 5-chloro-2-nitroaniline (2 g) was added. The mixture was then heated under reflux under argon for 3 hours then allowed to cool down. The resultant solid was collected by filtration , washed with ethanol then dried to give the title compound (236 g) as a solid. NMR: 6.3 8 (dd, 1H), 6.65 (m, 1H), 7.42 (m, 4H), 7.7 (m, 2H), 7.9 (d, 1H); MS: 327 (M+H)+.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux under argon for 3 hours
  3. temperatureto cool down
  4. filtrationThe resultant solid was collected by filtration
  5. washwashed with ethanol
  6. customthen dried

Sources & evidence

ORD record
ord-d6eb4c3c07404fe3874ffa5b0766a7d0
Source dataset
uspto-grants-2002_04
Patent number
US06369273B1

Reaction notes

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