Dimethyl Sulfoxide → HCID 54319431, compound

HRID 329600Notes

Reaction equation

HRID 329600 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:8]=[C:9]([CH:19]=[C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:21]=1[OH:22])[CH:10]=[C:11]1[CH2:16][CH2:15][O:14][N:13]([CH3:17])[C:12]1=[O:18])([CH3:6])([CH3:5])[CH3:4].[CH3:27]S(C)=O.CI>O>[C:3]([C:7]1[CH:8]=[C:9]([CH:19]=[C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:21]=1[O:22][CH3:27])[CH:10]=[C:11]1[CH2:16][CH2:15][O:14][N:13]([CH3:17])[C:12]1=[O:18])([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1309174-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]dihydro-2-methyl-2H-1,2-oxazin-3(4H)-one

Product 1

HCID 54319431HCID 54319431, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (0.33 g, 8.3 mmol), 60% in mineral oil dispersion, kept under nitrogen purge, was washed twice with 20 ml portions of hexane. Dimethyl sulfoxide (10 ml) was added, followed by the addition of 2.5 g (7.6 mmol) of dihydro-4-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2-methyl-2H-1,2-oxazin-3(4H)-one. Gas evolution was observed and the mixture became yellow following which an additional 5 ml of dimethyl sulfoxide was added. One hour later, 1.1 g (7.7 mmol) of methyl iodide was added and the mixture was stirred for 50 hours. The reaction mixture was diluted with 75 ml of water and precipitation occurred in the form of crystals which were collected and air dried to yield 3.3 g of crude product. Recrystallization from acetone-hexane afforded 1.85 g (5.4 mmol, 71%) of dihydro-4-(3,5-di-tert-butyl-4-methoxybenzylidene)-2-methyl-2H-1,2-oxazin-3(4H)-one having a melting point of 119°-121° C.

Workup

  1. custompurge
  2. washwas washed twice with 20 ml portions of hexane
  3. additionDimethyl sulfoxide (10 ml) was added
  4. additionwas added
  5. customwere collected
  6. customair dried
  7. customto yield 3.3 g of crude product
  8. customRecrystallization from acetone-hexane

Sources & evidence

ORD record
ord-8dbd4859f8b4459594a49646a7e97b47
Source dataset
uspto-grants-1990_01
Patent number
US04892870

Reaction notes

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