Benzothiazolone → 5-(2-Bromopropanoyl)-1,3-benzothiazol-2(3H)-one

HRID 1731319Notes

Reaction equation

HRID 1731319 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][CH:6]([CH3:10])[C:7](Br)=[O:8].[S:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[NH:13][C:12]1=[O:20]>C(=S)=S>[Br:5][CH:6]([CH3:10])[C:7]([C:18]1[CH:17]=[CH:16][C:15]2[S:11][C:12](=[O:20])[NH:13][C:14]=2[CH:19]=1)=[O:8]

Participants

5

Reactant 3

HCID 13625BenzothiazoloneHCID 79047Propanoyl bromide, 2-bromo-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 202287105-(2-Bromopropanoyl)-1,3-benzothiazol-2(3H)-oneYield 85.3%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a suspension of aluminum chloride (91.8 g) in carbon disulfide (200 ml) was added 2-bromopropionyl bromide (50 g) and 2-benzothiazolinone (20 g) and the resulting solution was refluxed for 6 hours with stirring. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo to give a residue, which was washed with diisopropyl ether and recrystallized from a mixture of ethyl acetate and diethyl ether to give 5-(2-bromopropionyl)-2-benzothiazolinone (32.3 g).

Workup

  1. temperaturethe resulting solution was refluxed for 6 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customto give a residue, which
  7. washwas washed with diisopropyl ether
  8. customrecrystallized from a mixture of ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-7e9d5cbc62234efba4e0f04d48b97d33
Source dataset
uspto-grants-1986_11
Patent number
US04621084

Reaction notes

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