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Water → N-[3-bromo-5-(4-nitrophenylsulphanyl)-phenyl]-N-methylacetamide

HRID 1603622
Notes
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Reaction equation

HRID 1603622 reaction equation
C1(S(N=N[C:12]2[CH:13]=[C:14]([N:19]([CH3:23])[C:20](=[O:22])[CH3:21])[CH:15]=[C:16]([Br:18])[CH:17]=2)(=O)=O)C=CC=CC=1.[K].[N+:25]([C:28]1[CH:33]=[CH:32][C:31]([SH:34])=[CH:30][CH:29]=1)([O-:27])=[O:26].O>CS(C)=O>[Br:18][C:16]1[CH:15]=[C:14]([N:19]([CH3:23])[C:20](=[O:22])[CH3:21])[CH:13]=[C:12]([S:34][C:31]2[CH:32]=[CH:33][C:28]([N+:25]([O-:27])=[O:26])=[CH:29][CH:30]=2)[CH:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 19605539N-[3-[2-(phenylsulphonyl)-diazenyl]-5-bromophenyl]-N-methylacetamideHCID 700026814Nitrothiophenol potassium salt

Product 1

HCID 19605546N-[3-bromo-5-(4-nitrophenylsulphanyl)-phenyl]-N-methylacetamideYield 103.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl Sulfoxide
Solvent

Conditions

Temperature
40 °C

Procedure

0.22 g (0.00055 mol) of N-[3-[2-(phenylsulphonyl)-diazenyl]-5-bromophenyl]-N-methylacetamide was dissolved in 15 ml of dimethyl sulphoxide, treated with 0.185 g (0.000825 mol) of 4-nitrothiophenol potassium salt and stirred at 40° C. for 18 hrs. The reaction mixture was poured into 300 ml of water, extracted with diethyl ether, the organic phase was washed with water and sat. sodium chloride solution, dried over MgSO4, filtered and the filtrate was freed from solvent. The residue was chromatographed on silica gel with 1% MeOH in dichloromethane. There was obtained 0.217 g (100%) of N-[3-bromo-5-(4-nitrophenylsulphanyl)-phenyl]-N-methylacetamide as a yellow oil. MS (EI): me/e=382, 380 (C15H13BrN2O3S+).

Workup

  1. extractionextracted with diethyl ether
  2. washthe organic phase was washed with water and sat. sodium chloride solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe residue was chromatographed on silica gel with 1% MeOH in dichloromethane

Sources & evidence

ORD record
ord-c4805e378a8f4743a97e08d34da669b8
Source dataset
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05990105

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes