Triethylsilane → 3-Methyl-6-(2-bromoethyl)benzothiazolinone

HRID 2254043Notes

Reaction equation

HRID 2254043 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11](=O)[CH2:12][Br:13])=[CH:10][C:5]=2[S:4](=[O:15])[CH2:3]1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][CH2:12][Br:13])=[CH:10][C:5]=2[S:4](=[O:15])[CH2:3]1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 867466573-Methyl-6-(bromoacetyl)benzothiazolinone

Product 1

HCID 701838363-Methyl-6-(2-bromoethyl)benzothiazolinone

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

In a 500-cm3 ground-necked flask surmounted by a condenser and placed in an oil bath, 42.9 g (0.15 mol) of 3-methyl-6-(bromoacetyl)benzothiazolinone are dissolved in 77 cm3 of trifluoroacetic acid with magnetic stirring and while the temperature is stabilized at 60° C. 52.7 cm3 (0.33 mol) of triethylsilane are introduced dropwise via a dropping funnel. After the addition, the heating is stopped and the mixture is left stirring vigorously for 30 hours. The reaction medium is hydrolyzed by pouring it into ice-cold water, and the precipitate obtained is drained and washed with water until the filtrate is neutral and then with hexane. The product is dried and recrystallized in cyclohexane.

Workup

  1. customIn a 500-cm3 ground-necked flask surmounted by a condenser
  2. customplaced in an oil bath
  3. customis stabilized at 60° C
  4. additionAfter the addition
  5. waitthe mixture is left
  6. stirringstirring vigorously for 30 hours
  7. additionby pouring it into ice-cold water
  8. customthe precipitate obtained
  9. washwashed with water until the filtrate
  10. customThe product is dried
  11. customrecrystallized in cyclohexane

Sources & evidence

ORD record
ord-4f4f025b36364d1189d24846cd4188c7
Source dataset
uspto-grants-1993_08
Patent number
US05234924

Reaction notes

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