N-bromobutanimide → 4-Bromo-1,3-benzothiazol-5-amine

HRID 2196192Notes

Reaction equation

HRID 2196192 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[N:7][C:6]=2[CH:10]=1.[Br:11]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[N:7][C:6]=2[C:10]=1[Br:11]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 70749Benzothiazol-5-amine

Product 1

HCID 224622234-Bromo-1,3-benzothiazol-5-amineYield 86.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 3 g of 5-aminobenzothiazole in 100 ml of acetonitrile at room temperature was treated with 3.5 g of N-bromosuccinimide and the resulting solution was stirred at room temperature for 4 hours. The solvent was removed under reduced pressure and the residue purified by silica gel chromatography (eluent cyclohexane/ethyl acetate 7:3) to afford 3.9 g of 5-amino-4-bromobenzothiazole as a pink solid. MS (ES+) 229/231 (MH+).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by silica gel chromatography (eluent cyclohexane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-acd3c265866944a19ce987aa0fab50dc
Source dataset
uspto-grants-2012_12
Patent number
US08338443B2

Reaction notes

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