4-Bromoaniline → N-(4-bromophenyl)-1,1-dioxo-1,2-benzothiazol-3-amine

HRID 2056072Notes

Reaction equation

HRID 2056072 reaction equation
Cl[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4](=[O:12])(=[O:11])[N:3]=1.[Br:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1>CC(C)=O>[Br:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:2]2[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[S:4](=[O:12])(=[O:11])[N:3]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 78074-BromoanilineHCID 64783Pseudosaccharin chloride

Product 1

HCID 716632N-(4-bromophenyl)-1,1-dioxo-1,2-benzothiazol-3-amineYield 94.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-chloro-1H-1λ6-benzo[d]isothiazole-1,1-dione (1.0 g, 0.00496 mol) in acetone (20 mL), 4-bromoaniline (1.71 g, 0.00992 mol) was added at once and the mixture was stirred for 15 min. The mixture was concentrated under reduced pressure and the residue was suspended in water (100 mL). The precipitate was collected by filtration, thoroughly washed with water and dried to yield 3-(4-bromoanilino)-1H-1λ6-benzo[d]isothiazole-1,1-dione (1.57 g, 0.00467 mol) as a white solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. filtrationThe precipitate was collected by filtration
  3. washthoroughly washed with water
  4. customdried

Sources & evidence

ORD record
ord-00465232e335489fab037d984d76c26d
Source dataset
uspto-grants-2008_02
Patent number
US07332497B2

Reaction notes

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