Bromine → HCID 86049084, compound

HRID 2235512Notes

Reaction equation

HRID 2235512 reaction equation
[C:1]1([CH3:23])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1)=[S:11].BrBr>C(Cl)(Cl)(Cl)Cl.O>[C:1]1([CH3:23])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][C:10]1[S:11][C:14]2[C:15]([N+:20]([O-:22])=[O:21])=[C:16]([CH3:19])[CH:17]=[CH:18][C:13]=2[N:12]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 86049082HCID 86049082, compound

Product 1

HCID 86049084HCID 86049084, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a mixture of 1-mesityl-3-(4-methyl-3-nitrophenyl)thiourea (500 mg, 1.52 mmol) in carbon tetrachloride (25 ml) was added dropwise bromine (0.097 ml, 1.90 mmol) in carbon tetrachloride (10 ml) over 1 h. The mixture was refluxed for 18 h and diluted with water. The aqueous solution was extracted with dichloromethane. The extract was washed with water and brine and concentrated under vacuum. The residue was triturated with ether. The resulting solid was collected by filtration to afford 225 mg of the title compound.

Workup

  1. temperatureThe mixture was refluxed for 18 h
  2. extractionThe aqueous solution was extracted with dichloromethane
  3. washThe extract was washed with water and brine
  4. concentrationconcentrated under vacuum
  5. customThe residue was triturated with ether
  6. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-38c1f10844e14e59896788aee80d9e11
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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