Sodium Hydroxide → 7-Bromobenzo[d]thiazol-5-amine

HRID 2300402Notes

Reaction equation

HRID 2300402 reaction equation
O.O.Cl[Sn]Cl.[N+:6]([C:9]1[CH:10]=[C:11]([Br:18])[C:12]2[S:16][CH:15]=[N:14][C:13]=2[CH:17]=1)([O-])=O.[OH-].[Na+]>Cl>[NH2:6][C:9]1[CH:10]=[C:11]([Br:18])[C:12]2[S:16][CH:15]=[N:14][C:13]=2[CH:17]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 227280317-Bromo-5-nitrobenzothiazole

Product 1

HCID 227280377-Bromobenzo[d]thiazol-5-amineYield 9,687.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of SnCl2.2H2O (0.5 g, 2.2 mol) in 5 mL of HCl was added 5-nitro-7-bromobenzothiazole (82 mg, 0.32 mmol) in a portion and the resulting reaction mixture was stirred for 1 h at 25° C. The reaction mixture was basified with aq. NaOH and extracted with EtOAc. Organic extracts were dried over Na2SO4 and concentrated in vacuo to yield 70 mg (31 mmol, 96%) of the desired product.

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with EtOAc
  3. dry with materialOrganic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8164c0d67e074ba4b25a916c50102245
Source dataset
uspto-grants-2002_12
Patent number
US06498177B2

Reaction notes

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