Methyl sulfate(1-) → 52793-97-2

HRID 460998Notes

Reaction equation

HRID 460998 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]1[CH:20]=[CH:19][C:6]([CH:7]=[C:8]2[CH:13]3[C:14]([CH3:16])([CH3:15])[C:10]([CH3:17])([CH2:11][CH2:12]3)[C:9]2=[O:18])=[CH:5][CH:4]=1.[S:22]([O-:27])([O:25][CH3:26])(=[O:24])=[O:23]>C(OCC)(=O)C>[CH3:26][O:25][S:22]([O-:27])(=[O:24])=[O:23].[O:18]=[C:9]1[C:8](=[CH:7][C:6]2[CH:5]=[CH:4][C:3]([N+:2]([CH3:26])([CH3:1])[CH3:21])=[CH:20][CH:19]=2)[CH:13]2[C:14]([CH3:16])([CH3:15])[C:10]1([CH3:17])[CH2:11][CH2:12]2

Participants

4

Reactant 2

HCID 4694097Methyl sulfate(1-)HCID 681253453-[[4-(Dimethylamino)phenyl]methylene]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

Product 1

HCID 2098154852793-97-2Yield 140.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

750 g of 4-dimethylamino benzylidene camphor (prepared in Example 1) and 334 g of methyl sulfate are progressively heated to reflux in ethyl acetate. An exothermic precipitation suddenly occurs and when it has abated the reaction mixture is then heated for three hours at reflux. A pale yellow solid precipitates which is then filtered, washed with ethyl acetate and recrystallized in a benzene-acetonitrile mixture, yielding 866 g of white product melting at 20° C.

Workup

  1. customAn exothermic precipitation
  2. temperatureis then heated for three hours
  3. temperatureat reflux
  4. customA pale yellow solid precipitates which
  5. filtrationis then filtered
  6. washwashed with ethyl acetate
  7. customrecrystallized in a benzene-acetonitrile mixture

Sources & evidence

ORD record
ord-cc72ffd0a07d4b05a11cd814e9743312
Source dataset
uspto-grants-1977_12
Patent number
US04061730

Reaction notes

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