Water → 4-(4-Amino-phenylsulfanyl)-N-(5-bromo-pyridin-2-yl)-3-nitro-benzamide

HRID 605323Notes

Reaction equation

HRID 605323 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([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)=[N:6][CH:7]=1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=1.O.O.O.C([O-])(=O)C.[Na+].O>C(O)C>[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28][C:13]2[CH:14]=[CH:15][C:10]([C:9]([NH:8][C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=3)=[O:20])=[CH:11][C:12]=2[N+:17]([O-:19])=[O:18])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 145104-AminothiophenolHCID 5023018N-(5-bromopyridin-2-yl)-4-chloro-3-nitrobenzamideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 670400914-(4-Amino-phenylsulfanyl)-N-(5-bromo-pyridin-2-yl)-3-nitro-benzamideYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the product of Example 364A (24.2 g, 0.0678 mol), 4-amino-benzenethiol (12.7 g, 0.102 mol, 1.5 equiv.), and sodium acetate trihydrate (46.1 g, 0.339 mol, 5.0 equiv.) in 500 mL of ethanol was heated under reflux under nitrogen with stirring for 2 hours. The reaction mixture was then allowed to cool to room temperature and 200 mL of water added. The mixture was stirred for 30 minutes, filtered, and dried in vacuo to give the title compound (29.8 g, 99%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under nitrogen
  3. stirringThe mixture was stirred for 30 minutes
  4. filtrationfiltered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-de81cd1c60ab4523be21d9c2583348bd
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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