Water → 2-Formyl-4,5-dimethoxyphenyl dimethylsulphamate

HRID 420864

Reaction equation

HRID 420864 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:8]([OH:13])=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=[O:7].C(=O)([O-])[O-].[K+].[K+].[CH3:20][N:21]([CH3:26])[S:22](Cl)(=[O:24])=[O:23].O>CN(C=O)C>[CH3:20][N:21]([CH3:26])[S:22](=[O:24])(=[O:23])[O:13][C:8]1[CH:9]=[C:10]([O:11][CH3:12])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH:6]=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 83372Dimethylsulphamoyl chlorideHCID 109869082-Hydroxy-4,5-dimethoxybenzaldehyde

Product 1

HCID 866430082-Formyl-4,5-dimethoxyphenyl dimethylsulphamateYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

Dissolve 16.2 g (0.0889 mol) of 3,4-dimethoxy-6-hydroxybenzaldehyde in 80 ml of DMF. Cool to 10° C. and add in portions 24.6 g (0.178 mol) of potassium carbonate. Allow to return to ambient temperature and stir for 30 minutes. Cool to approximately 10° C. and pour in dropwise 10.1 ml (0.093 mol) of N,N-dimethylsulphamoyl chloride. Allow to return to ambient temperature and stir for 2 h. Pour the reaction mixture into 600 g of water and ice and stir for 1 h at ambient temperature. The precipitate formed is filtered off and washed 3 times with 50 ml of water each time and then dried in vacuo. 21.3 g of title product are obtained.

Workup

  1. customto return to ambient temperature
  2. temperatureCool to approximately 10° C.
  3. customto return to ambient temperature
  4. stirringstir for 2 h
  5. stirringstir for 1 h at ambient temperature
  6. customThe precipitate formed
  7. filtrationis filtered off
  8. washwashed 3 times with 50 ml of water each time
  9. customdried in vacuo

Sources & evidence

ORD record
ord-c010bd7aa97d4a2297e58994385f2b9a
Source dataset
uspto-grants-2012_01
Patent number
US08097720B2

Linked notes

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