Hydrogen Bromide → 2-Bromo-7-nitrobenzo[d]thiazole

HRID 2235502Notes

Reaction equation

HRID 2235502 reaction equation
[N+:1]([C:4]1[C:12]2[S:11][C:10](N)=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[BrH:14].BrBr.N([O-])=O.[Na+].[OH-].[Na+]>C(O)(=O)C.O>[Br:14][C:10]1[S:11][C:12]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=[CH:7][C:8]=2[N:9]=1

Participants

8

Reactant 5

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 24408BromineHCID 43257247-Nitro-1,3-benzothiazol-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 685819982-Bromo-7-nitrobenzo[d]thiazole

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a suspension of 7-nitro-1,3-benzothiazol-2-ylamine (1.80 g, 9.22 mmol) in acetic acid (AcOH) (20 ml) was added 48% hydrogen bromide in H2O (10 ml) with ice-cooling. Bromine (0.157 ml) was added dropwise followed by sodium nitrite (177 mg, 23.9 mmol) in H2O (1 ml). The temperature was kept at 0 to 5° C. The mixture was stirred for 2 h with ice-cooling and then was made alkaline by dropwise addition of 6N NaOH solution. The resulting precipitate was collected by filtration, washed with water and dried under vacuum to give 1.91 g of the title compound.

Workup

  1. temperaturecooling
  2. customwas kept at 0 to 5° C
  3. temperaturecooling
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-9078bbd7fa42402fa31cf0cd143bc667
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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