Sodium Hydroxide → 2,4-Dibromo-6-methylbenzothiazole

HRID 1769020

Reaction equation

HRID 1769020 reaction equation
N[C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([Br:12])[C:5]=2[N:6]=1.[Br:13](O)(=O)=O.BrBr.N([O-])=O.[Na+].[OH-].[Na+]>>[Br:13][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([Br:12])[C:5]=2[N:6]=1

Participants

6

Reactant 5

HCID 14798Sodium HydroxideHCID 24408BromineHCID 24445Bromic acidHCID 32786344-Bromo-6-methyl-1,3-benzothiazol-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 189465492,4-Dibromo-6-methylbenzothiazole

Procedure

4.7 g of 2-amino-4-bromo-6-methylbenzothiazole, 14 ml of 48% bromic acid solution and 10 g of bromine were introduced into a reaction vessel while keeping the temperature at 10° C. To this mixture was slowly added dropwise 10 ml of aqueous solution containing 3.5 g of sodium nitrite at 0° C. and the whole mixture was stirred for 2 hours. Then, 15 ml of 40% sodium hydroxide solution was slowly added dropwise while keeping the temperature below 20° C. and the reaction mixture was stirred for one hour and extracted with diethyl ether. The extract was dried with anhydrous sodium sulfate and evaporated to obtain the title compound in the form of transparent liquid (Yield: 91%).

Workup

  1. customat 10° C
  2. customthe temperature below 20° C.
  3. stirringthe reaction mixture was stirred for one hour
  4. extractionextracted with diethyl ether
  5. dry with materialThe extract was dried with anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-e2bb665e554a4ed2bafa8435ae6d0eff
Source dataset
uspto-grants-1995_01
Patent number
US05380735

Linked notes

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