Hydrochloric Acid → N-(3-Bromo-phenyl)-4-(3-hydroxy-phenylsulfanyl)-3-nitro-benzamide

HRID 605123Notes

Reaction equation

HRID 605123 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][C:13](Cl)=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[OH:21][C:22]1[CH:23]=[C:24]([SH:28])[CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][C:13]([S:28][C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([OH:21])[CH:23]=3)=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 1368133N-(3-bromophenyl)-4-chloro-3-nitrobenzamideHCID 27366133-Hydroxybenzenethiol

Product 1

HCID 67040801N-(3-Bromo-phenyl)-4-(3-hydroxy-phenylsulfanyl)-3-nitro-benzamideYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(3-Bromo-phenyl)-4-chloro-3-nitro-benzamide (from Example 26A) (0.356 g, 1.0 mmol), 3-hydroxythiophenol (0.126 g, 1.0 mmol) and cesium carbonate (0.65 g, 2.0 mmol) in N,N-dimethylformamide (5 mL) was heated to 95° C. for 3 hours. After cooling to room temperature the mixture was poured into ice water (20 mL) and the resultant solution acidified with 1N aqueous hydrochloric acid. The solution was then extracted with ethyl acetate (3×10 mL), the combined extracts dried over magnesium sulfate, filtered and concentrated under vacuum to provide the title compound (0.430 g, 97%).

Workup

  1. extractionThe solution was then extracted with ethyl acetate (3×10 mL)
  2. dry with materialthe combined extracts dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8fdd92dbf8994060aeacb43754c9b929
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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