Hydrochloric Acid → 7-Bromo-benzo[d]isothiazol-5-ylamine

HRID 389470Notes

Reaction equation

HRID 389470 reaction equation
[Br:1][C:2]1[C:10]2[S:9][N:8]=[CH:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-])=O)[CH:3]=1.Cl>C(O)C.[Fe]>[Br:1][C:2]1[C:10]2[S:9][N:8]=[CH:7][C:6]=2[CH:5]=[C:4]([NH2:11])[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66759851HCID 66759851, compound

Product 1

HCID 667606927-Bromo-benzo[d]isothiazol-5-ylamineYield 56%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7-bromo-5-nitro-benzo[d]isothiazole (1.0 g, 3.9 mmol) and iron powder (1.0 g, 19 mmol) in ethanol (40 mL) was heated to reflux with vigorous stirring. An aqueous 0.1 N hydrochloric acid (10 mL, 1 mmol) solution was added and the reaction continued until TLC showed no starting material. The reaction mixture was cooled to RT and filtered. The filtrate was concentrated and aqueous sodium carbonate was added to the residue until it became basic. This mixture was filtered through Celite, washing with ethyl acetate. The organic layer was separated, washed with water, dried over anhydrous sodium sulfate and concentrated to give 500 mg (56%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 8.8 (s, 1H), 7.2 (s, 1H), 7.1 (s, 1H), 3.82 (br. s, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux with vigorous stirring
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. additionaqueous sodium carbonate was added to the residue until it
  6. filtrationThis mixture was filtered through Celite
  7. washwashing with ethyl acetate
  8. customThe organic layer was separated
  9. washwashed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-6d655562fa0d41e1b89203cf9d38a70e
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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