Dimethyl Sulfate → HCID 13565195, compound

HRID 904906Notes

Reaction equation

HRID 904906 reaction equation
[CH2:1]([NH:5][CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]=1)[C:7]#[N:8])[CH:2]([CH3:4])[CH3:3].S(OC)(O[CH3:26])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([N:5]([CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]=1)[C:7]#[N:8])[CH3:26])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 13565194HCID 13565194, compound

Product 1

HCID 13565195HCID 13565195, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of α-(N-isobutylamino)-3-phenoxybenzeneacetonitrile (28.0 g; 0.1 mole), dimethyl sulfate (12.6 g; 0.1 mole), anhydrous potassium carbonate (15.0 g) and anhydrous acetone (100 ml) was stirred at a temperature of 50° C. for a period of 16 hours. The mixture was filtered and the solvent was removed from the filtrate by distillation under reduced pressure. The residue was treated with anhydrous diethyl ether, the etherial solution was separated and the ether was evaporated to give α-(N-isobutyl-N-methylamino)-3-phenoxybenzeneacetonitrile as a yellow oil. Proton nuclear magnetic resonance spectrum (d6 -acetone; δ in ppm): 0.85 (6H, d of d); 1.83 (1H, m); 2.23 (3H, s); 5.19 (1H, s); 7.0-7.5 (9H, m).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was removed from the filtrate by distillation under reduced pressure
  3. additionThe residue was treated with anhydrous diethyl ether
  4. customthe etherial solution was separated
  5. customthe ether was evaporated

Sources & evidence

ORD record
ord-97e697c9df584afbb4498d015be1ea69
Source dataset
uspto-grants-1983_12
Patent number
US04420614

Reaction notes

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