Ethyl Acetate → HCID 131715063, compound

HRID 236544Notes

Reaction equation

HRID 236544 reaction equation
[ClH:1].[CH3:2][S:3][C:4]1[CH:23]=[CH:22][C:7]2[O:8][CH2:9][C:10]3[CH:21]=[CH:20][CH:19]=[CH:18][C:11]=3[C:12]([CH2:14][N:15]([CH3:17])[CH3:16])([OH:13])[C:6]=2[CH:5]=1.C(=O)(O)[O-:25].[Na+].[OH2:29].C(OCC)(=O)C>FC(F)(F)C(O)=O>[ClH:1].[CH3:2][S:3]([C:4]1[CH:23]=[CH:22][C:7]2[O:8][CH2:9][C:10]3[CH:21]=[CH:20][CH:19]=[CH:18][C:11]=3[C:12]([CH2:14][N:15]([CH3:17])[CH3:16])([OH:13])[C:6]=2[CH:5]=1)(=[O:25])=[O:29]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 86585896Sodium bicarbonate waterHCID 131715064HCID 131715064, compound

Product 1

HCID 131715063HCID 131715063, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Conditions

Temperature
-30 °C

Procedure

2-Methylthio-11-dimethylaminomethyl-6,11-dihydrodibenz(b,e)oxepin-11-ol, hydrochloride (1.404 g, 4 mmole) is dissolved in 8 ml of trifluoroacetic acid and cooled to -30° C. 8.6 ml of 4M solution of peroxytrifluoro acetic acid in trifluoroacetic acid is added dropwise. The solution is allowed to stay at room temperature. A controlled exothermic reaction starts. After 30 minutes the reaction is complete (the reaction is readily followed by NMR). The solvent is poured into an excess solid sodiumbicarbonate-water mixture and ethyl acetate. The organic extract is washed with 10% sodium bicarbonate and dried over anhydrous sodium sulphate. The desired compound, 2-methylsulfonyl-11-dimethylaminomethyl-6,11-dihydrodibenz(b,e)oxepin-11-ol, hydrochloride, is isolated. M M.p. 247° C. (compound 7:1)

Workup

  1. customto stay at room temperature
  2. customA controlled exothermic reaction
  3. extractionThe organic extract
  4. washis washed with 10% sodium bicarbonate
  5. dry with materialdried over anhydrous sodium sulphate

Sources & evidence

ORD record
ord-95e9be88ee814d229a605420a6d14a0c
Source dataset
uspto-grants-1987_02
Patent number
US04645758

Reaction notes

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