Bromoacetyl chloride → 6-(Bromoacetyl)benzothiazolinone

HRID 2254039Notes

Reaction equation

HRID 2254039 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[S:5]1(=[O:14])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[CH:6]1.[Br:15][CH2:16][C:17](Cl)=[O:18]>CN(C)C=O>[Br:15][CH2:16][C:17]([C:11]1[CH:12]=[CH:13][C:8]2[N:7]=[CH:6][S:5](=[O:14])[C:9]=2[CH:10]=1)=[O:18]

Participants

5

Reactant 3

HCID 89602Bromoacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 53400715Benzothiazolinone

Product 1

HCID 1317178296-(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. 30.2 g (0.2 mol) of benzothiazolinone 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 introduced 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 copiously with water and dried. The product is recrystallized in dioxane.

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 copiously with water
  10. customdried
  11. customThe product is recrystallized in dioxane

Sources & evidence

ORD record
ord-b72ed2c2277b4406a9833e50b4115da0
Source dataset
uspto-grants-1993_08
Patent number
US05234924

Reaction notes

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