Dimethyl Sulfate → HCID 73473422, compound

HRID 1492047Notes

Reaction equation

HRID 1492047 reaction equation
[N+:1]([CH2:4][C:5]([S-:7])=S)([O-:3])=[O:2].[K+].[K+].[N+]([CH2:13]C([S-])=S)([O-])=O.[CH:17]([NH2:23])([C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:18].S(OC)(OC)(=O)=O>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1>[CH3:18][CH:17]([NH:23][C:5]([S:7][CH3:13])=[CH:4][N+:1]([O-:3])=[O:2])[C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 5209072-Butanamine, 3,3-dimethyl-HCID 18954385HCID 18954385, compound

Product 1

HCID 73473422HCID 73473422, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 5963Benzyltrimethylammonium chlorideCatalyst

Conditions

Temperature
60 °C

Procedure

To an aqueous solution of dipotassium nitrodithioacetate (300 g 15% by weight) was added pinacolylamine (32 g) over 1 hour. After heating to 60° C. and maintaining this temperature for 4 hours, the reaction mixture was cooled to ambient temperatures and stirred overnight. Benzyltrimethylammonium chloride (3 g ), was then charged, followed by dimethyl sulphate (66 g) over one hour. After stirring overnight, the reaction mixture was extracted three times with 50ml aliquots of dichloromethane. After drying over MgSO4, the combined organic phases were concentrated and the residue recrystallised from 2-propanol to give 13 g (33%) of the title compound (m.p. 69° C.) which is believed to be novel.

Workup

  1. temperaturemaintaining this temperature for 4 hours
  2. temperaturethe reaction mixture was cooled to ambient temperatures
  3. stirringAfter stirring overnight
  4. extractionthe reaction mixture was extracted three times with 50ml aliquots of dichloromethane
  5. dry with materialAfter drying over MgSO4
  6. concentrationthe combined organic phases were concentrated
  7. customthe residue recrystallised from 2-propanol

Sources & evidence

ORD record
ord-7848d6c14e964e2a875767bd7741ab39
Source dataset
uspto-grants-1994_12
Patent number
US05371247

Reaction notes

Loading…