Trifluoroacetic acid → 6-Benzylbenzothiazolinone

HRID 1091073Notes

Reaction equation

HRID 1091073 reaction equation
[C:1]([C:9]1[CH:18]=[CH:17][C:12]2[N:13]=[CH:14][S:15](=[O:16])[C:11]=2[CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[CH2:1]([C:9]1[CH:18]=[CH:17][C:12]2[N:13]=[CH:14][S:15](=[O:16])[C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 1317171596-Benzoylbenzothiazolinone

Product 1

HCID 1317171586-Benzylbenzothiazolinone

Procedure

10.2 g (0.04 mole) of 6-benzoylbenzothiazolinone are weighed into a 105-cm: flask. 45.6 g (0.4 mole) of trifluoroacetic acid are added via a dropping funnel equipped with a teflon tap. 10.5 g (0.09 mole) of triethylsilane are added dropwise with magnetic stirring and while cooling by means of a bath of ice-cold water. A calcium chloride guard tube is fitted and stirring is continued for fifteen hours at room temperature. The reaction mixture is poured with stirring into 500 cm3 of ice-cold water. The precipitate obtained is drained and washed with water until the washing liquors are neutral. The product is dried and recrystallized in toluene.

Workup

  1. temperaturewhile cooling by means of a bath of ice-cold water
  2. customA calcium chloride guard tube is fitted
  3. stirringstirring
  4. waitis continued for fifteen hours at room temperature
  5. additionThe reaction mixture is poured
  6. customThe precipitate obtained
  7. washwashed with water until the washing liquors
  8. customThe product is dried
  9. customrecrystallized in toluene

Sources & evidence

ORD record
ord-60cd9e77a69348ecb321f5aa6c7f743a
Source dataset
uspto-grants-1992_01
Patent number
US05084469

Reaction notes

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