Sodium Methoxide → HCID 18963924, compound

HRID 257058Notes

Reaction equation

HRID 257058 reaction equation
[CH3:1][O-:2].[Na+].[C:4]1([CH2:10][CH2:11][CH2:12][NH:13][S:14]([C:17]2[C:22](OC)=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:25][C:26]([O:28]CC)=O)(=[O:16])=[O:15])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C1(C)C=CC=CC=1.CCOC(C)=O.O>[CH3:1][O:2][C:20]1[CH:21]=[CH:22][C:17]2[S:14](=[O:15])(=[O:16])[N:13]([CH2:12][CH2:11][CH2:10][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:26](=[O:28])[CH2:25][C:18]=2[CH:19]=1

Participants

6

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 18963956HCID 18963956, compound

Product 1

HCID 18963924HCID 18963924, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium Methoxide (280 mg, 5.1 mmol) and ethyl 2-[(N-3-phenylpropylamino)-sulfonyl]-3-methoxyphenylacetate (2.0 g, 5.1 mmol) are dissolved in toluene (200 mL) and the resulting solution is refluxed for 24 hours. An additional portion of sodium methoxide (60 mg, 1.1 mmol) is added and the reaction is once again refluxed for 24 hours. The reaction mixture is subsequently diluted with EtOAc (200 mL) and H2O (200 mL). The organic phase is then washed with saturated NaCl solution (2×200 mL), dried over MgSO4 and concentrated in vacuo to give 6-methoxy-2-(3-phenylpropyl)-3-oxo-3,4-dihydro-2H-1,2-benzothiazine-1,1-dioxide.

Workup

  1. temperaturethe resulting solution is refluxed for 24 hours
  2. temperaturethe reaction is once again refluxed for 24 hours
  3. washThe organic phase is then washed with saturated NaCl solution (2×200 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-39aeb0579cd14f89b0d8f5983c05d692
Source dataset
uspto-grants-1993_11
Patent number
US05260316

Reaction notes

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