Hydrochloric Acid → 4-(3-Amino-phenylsulfanyl)-N-(3-bromo-phenyl)-3-nitro-benzamide

HRID 605143Notes

Reaction equation

HRID 605143 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.[NH2:21][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>[NH2:21][C:22]1[CH:23]=[C:24]([S:28][C:13]2[CH:14]=[CH:15][C:10]([C:9]([NH:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=3)=[O:20])=[CH:11][C:12]=2[N+:17]([O-:19])=[O:18])[CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 315773-AminothiophenolHCID 1368133N-(3-bromophenyl)-4-chloro-3-nitrobenzamide

Product 1

HCID 670402744-(3-Amino-phenylsulfanyl)-N-(3-bromo-phenyl)-3-nitro-benzamideYield 107.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(3-Bromo-phenyl)-4-chloro-3-nitro-benzamide (from Example 26A) (2.13 g, 6.0 mmol), 3-aminothiophenol (0.75 g, 6.0 mmol) and cesium carbonate (4.0 g, 12.0 mmol) in N,N-dimethylformamide (20 mL) was heated to 95° C. for 3 hours. After cooling to room temperature the mixture was poured into ice water (100 mL) and the resultant solution adjusted to pH 6 with 1N aqueous hydrochloric acid. The solution was then extracted with ethyl acetate (3×50 mL), the combined extracts dried over sodium sulfate, filtered and concentrated under vacuum to provide the title compound (2.87 g, 99%).

Workup

  1. extractionThe solution was then extracted with ethyl acetate (3×50 mL)
  2. dry with materialthe combined extracts dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4a1adf56b40045a2b612e07f130f2146
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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