Ammonia → 6-Bromo-1,3-benzothiazole

HRID 473780Notes

Reaction equation

HRID 473780 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:14]=[CH:13][C:9]2[N:10]=[CH:11][S:12][C:8]=2[CH:7]=1.N.[BrH:16]>O.Cl.[Cu]Br>[Br:16][C:6]1[CH:14]=[CH:13][C:9]2[N:10]=[CH:11][S:12][C:8]=2[CH:7]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 260Hydrogen BromideHCID 682886-AminobenzothiazoleHCID 23668193Sodium Nitrite

Product 1

HCID 27951716-Bromo-1,3-benzothiazole

Reagents, catalysts & solvents 3

HCID 24593copper(I) bromideCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of sodium nitrite (0.147 g, 2.1 mmol) in water (1.0 mL) was slowly added to a suspension of 6-aminobenzothiazole (0.30 g, 2.0 mmol) in HBr (48% in water, 3 mL) at 0° C. and then the mixture was stirred at room temperature for 30 min. The formed solution was then slowly added to a solution of copper (I) bromide (0.435 g, 3.0 mmol) in HCl (conc., 5 mL) at 0° C. After the addition, the mixture was stirred at 60° C. for 1.5 h. Cooled down, and the reaction mixture was basified with excess ammonia and extracted with diethyl ether. The combined extract was washed with water, brine, dried and concentrated. The 6-bromobenzothiazole (0.26 g) was obtained by Combiflash and then converted to the final compound using procedures analogous to those for example 1, MS(ESI): (M+H)+=413.1.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred at 60° C. for 1.5 h
  3. temperatureCooled down
  4. extractionextracted with diethyl ether
  5. extractionThe combined extract
  6. washwas washed with water, brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d6affce9e9f54e85b9bee46d51d3da8d
Source dataset
uspto-grants-2014_01
Patent number
US08637497B2

Reaction notes

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