Triethylsilane → HCID 19752233, compound

HRID 483333Notes

Reaction equation

HRID 483333 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:17]=[CH:16][C:10]2[NH:11][C:12](=[O:15])[CH2:13][O:14][C:9]=2[CH:8]=1)=O.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:7]1[CH:17]=[CH:16][C:10]2[NH:11][C:12](=[O:15])[CH2:13][O:14][C:9]=2[CH:8]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 197522327-(4-bromoBUTYRYL)2,3-dihydro 3-oxo 1,4-benzoxazine

Product 1

HCID 19752233HCID 19752233, compoundYield 80%

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, 40.8 g (0.15 mol) of 7-(4-bromoBUTYRYL)2,3-dihydro 3-oxo 1,4-benzoxazine described in European Patent Application EP 0223674 are dissolved in 90 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 then 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 absolute ethanol. Yield: 80%

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 then 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 absolute ethanol

Sources & evidence

ORD record
ord-d5ce65142c63416bbe6dfca6435478cc
Source dataset
uspto-grants-1993_07
Patent number
US05225409

Reaction notes

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