Ammonia → 6-Bromo-1,3-benzothiazole

HRID 2240512Notes

Reaction equation

HRID 2240512 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-ebd05bce4dc74b389502fedb6bd93e3b
Source dataset
uspto-grants-2010_05
Patent number
US07723349B2

Reaction notes

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