Ethyl Acetate → HCID 22735323, compound

HRID 1279216Notes

Reaction equation

HRID 1279216 reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][NH:9][C:8]2[CH:11]=[CH:12][C:13]([C:15]([F:18])([F:17])[F:16])=[CH:14][C:7]=2[S:6]1)=O.C(=O)([O-])O.[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.O1CCCC1>[OH:2][CH2:3][CH:5]1[CH2:10][NH:9][C:8]2[CH:11]=[CH:12][C:13]([C:15]([F:18])([F:17])[F:16])=[CH:14][C:7]=2[S:6]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 22735305HCID 22735305, compound

Product 1

HCID 22735323HCID 22735323, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-methoxycarbonyl-7-trifluoromethyl-3,4-dihydro-2H-[1,4]benzothiazine in 50 ml of toluene and about 10 ml of tetrahydrofuran, kept under argon. The reaction mixture is heated for 1 hour under reflux, and then after returning to 20° C. is hydrolysed with 70 ml of a saturated aqueous sodium hydrogen carbonate solution and 40 ml of ethyl acetate. The insoluble matter is removed by filtration and the filtrate is separated after settling out, the organic phase is dried over magnesium sulphate and concentrated to dryness under reduced pressure (2 kPa). The yellow oil obtained is chromatographed on 35 g of 20-45 μm silica gel contained in a column 2 cm in diameter, eluting with an ethyl acetate and cyclohexane mixture (75-25 by volume). 0.72 g of 2-hydroxymethyl-7-trifluoromethyl-3,4-dihydro-2H-[1,4]benzothiazine is thus obtained in the form of a yellow solid melting at 80° C.

Workup

  1. temperatureThe reaction mixture is heated for 1 hour
  2. temperatureunder reflux
  3. customafter returning to 20° C.
  4. customThe insoluble matter is removed by filtration
  5. customthe filtrate is separated
  6. dry with materialthe organic phase is dried over magnesium sulphate
  7. concentrationconcentrated to dryness under reduced pressure (2 kPa)
  8. customThe yellow oil obtained
  9. customis chromatographed on 35 g of 20-45 μm silica gel
  10. washeluting with an ethyl acetate and cyclohexane mixture (75-25 by volume)

Sources & evidence

ORD record
ord-165928f897bd402d92d76e7d563e6782
Source dataset
uspto-grants-2002_09
Patent number
US06448241B1

Reaction notes

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