Potassium Hydroxide → 2-(4-aminobenzenesulphonyl)-3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine

HRID 1018476Notes

Reaction equation

HRID 1018476 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH:19]([CH3:20])[CH:18]=[C:17]([CH3:21])[CH:16]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH3:30])=[CH:24][CH:23]=3)[O:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=O)C.[OH-].[K+]>CO.ClCCl>[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:14]2[CH:19]([CH3:20])[CH:18]=[C:17]([CH3:21])[CH:16]([C:22]3[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH3:30])=[CH:26][CH:27]=3)[O:15]2)(=[O:12])=[O:13])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 98455822-(4-acetamidobenzenesulphonyl)-3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine

Product 1

HCID 117736522-(4-aminobenzenesulphonyl)-3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of 2-(4-acetamidobenzenesulphonyl)-3, 6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl) -2H-1,2-oxazine (0.153 g) and powdered potassium hydroxide (40mg) in methanol (5 ml) was-heated under reflux for 24 h. The cooled mixture was diluted with dichloromethane and the solution washed with water. The dichloromethane solution was separated, dried over magnesium sulphate, filtered and evaporated to dryness. The residual oil was purified by chromatography on silica using ethyl acetate:n-hexane 3:2 as eluant to give 2-(4-aminobenzenesulphonyl)-3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine as a colourless foam. 1H NMR (CDCl3) δ 1.44(9H, m), 4.02(2H, q), 4.13(2H, br s), 4.44 (1H, m), 5.02(1H, br s), 5.70(1H, m), 6.61(2H, d), 6.83(2H, d), 7.13(2H, d), 7.65(2H, d).

Workup

  1. temperaturewas-heated
  2. temperatureunder reflux for 24 h
  3. washthe solution washed with water
  4. customThe dichloromethane solution was separated
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residual oil was purified by chromatography on silica

Sources & evidence

ORD record
ord-d47fad984ca1487092ab21090d320441
Source dataset
uspto-grants-2002_11
Patent number
US06482824B1

Reaction notes

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