Bromoacetyl chloride → 3-Methyl-6-(bromoacetyl)benzothiazolinone

HRID 2254042Notes

Reaction equation

HRID 2254042 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:8](=[O:15])[CH2:7]1.[Br:16][CH2:17][C:18](Cl)=[O:19]>CN(C)C=O>[CH3:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:18](=[O:19])[CH2:17][Br:16])=[CH:14][C:9]=2[S:8](=[O:15])[CH2:7]1

Participants

5

Reactant 3

HCID 89602Bromoacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 20026384N-methylbenzothiazolone

Product 1

HCID 867466573-Methyl-6-(bromoacetyl)benzothiazolinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

210 g (1.60 mol) of aluminum chloride are introduced into a 500-cm3 ground-necked flask surmounted by a condenser, and 43 cm3 of dimethylformamide are then added dropwise and with magnetic stirring via a dropping funnel. 33 g (0.20 mol) of 3-methylbenzothiazolinone are then added and, while the reaction medium homogenizes, the temperature is stabilized at 70° C. using an oil bath. 19.8 cm3 (0.24 mol) of bromoacetyl chloride are then added gradually. After the addition, the mixture is left stirring for one hour at a temperature of 70° C. The reaction medium is hydrolyzed by pouring it onto crushed ice and the precipitate obtained is drained, washed with water until the filtrate is neutral and dried. The product is recrystallized in 95° strength alcohol.

Workup

  1. customsurmounted by a condenser
  2. customis stabilized at 70° C.
  3. additionAfter the addition
  4. waitthe mixture is left
  5. stirringstirring for one hour at a temperature of 70° C
  6. additionby pouring it
  7. customonto crushed ice
  8. customthe precipitate obtained
  9. washwashed with water until the filtrate
  10. customdried
  11. customThe product is recrystallized in 95° strength alcohol

Sources & evidence

ORD record
ord-f83669a1fe1d4c31ac42ea25a41b0ddf
Source dataset
uspto-grants-1993_08
Patent number
US05234924

Reaction notes

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