Bromine → N2-Mesityl-4-methyl-N7,N7-dipropyl-1,3-benzothiazole-2,7-diamine

HRID 2235509Notes

Reaction equation

HRID 2235509 reaction equation
[CH2:1]([N:4]([CH2:25][CH2:26][CH3:27])[C:5]1[CH:6]=[CH:7][C:8]([CH3:24])=[C:9]([NH:11][C:12]([NH:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])=[S:13])[CH:10]=1)[CH2:2][CH3:3].BrBr>C(Cl)(Cl)(Cl)Cl.O>[C:20]1([CH3:21])[CH:19]=[C:18]([CH3:22])[CH:17]=[C:16]([CH3:23])[C:15]=1[NH:14][C:12]1[S:13][C:10]2[C:5]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:25][CH2:26][CH3:27])=[CH:6][CH:7]=[C:8]([CH3:24])[C:9]=2[N:11]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 866129911-(5-Dipropylamino-2-methylphenyl)-3-mesitylthiourea

Product 1

HCID 58896415N2-Mesityl-4-methyl-N7,N7-dipropyl-1,3-benzothiazole-2,7-diamineYield 39.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a mixture of 1-(5-dipropylamino-2-methylphenyl)-3-mesitylthiourea (100 mg, 0.261 mmol) in carbon tetrachloride (10 ml) was added dropwise bromine (0.015 ml, 0.287 mmol) in carbon tetrachloride (5 ml) over 30 min. 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 purified by chromatography eluting with 10% AcOEt in n-hexane to afford 39 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 purified by chromatography
  6. washeluting with 10% AcOEt in n-hexane

Sources & evidence

ORD record
ord-a6e937661b2343fe881f9151477098c8
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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