Dehydrothio-4-toluidine → 2-Bromo-4-(6-methyl-2-benzothiazolyl)benzenamine

HRID 1636557Notes

Reaction equation

HRID 1636557 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[Br:18]Br>ClCCl>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:6][C:7]=1[Br:18]

Participants

4

Reactant 2

HCID 7087Dehydrothio-4-toluidineHCID 24408Bromine

Product 1

HCID 3879492-Bromo-4-(6-methyl-2-benzothiazolyl)benzenamineYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4'-Aminophenyl)-6-methylbenzothiazole (0.6 g, 2.5 mmol) was treated with bromine (0.403 g, 2.5 mmol) in dichloromethane according to the above-described general procedure for bromination. Crude product was purified by flash chromatography on silica gel, using ethyl acetate-hexane (1:3) as eluent, to give brown small crystals (0.68 g, 85.3%), m.p. 187.9-189.5° C.

Workup

  1. customCrude product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-3ebd9a092d444e0db1f15463225f7f7f
Source dataset
uspto-grants-2000_03
Patent number
US06034246

Reaction notes

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