Dimethyl Sulfate → HCID 19832668, compound

HRID 2051094Notes

Reaction equation

HRID 2051094 reaction equation
[CH3:1][O:2][N:3]([CH3:26])[C:4](=[O:25])[C:5]1[CH:10]=[C:9]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[NH:13][C:12]2=[O:22])[C:8]([F:23])=[CH:7][C:6]=1[Cl:24].S(OC)(O[CH3:31])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH3:1][O:2][N:3]([CH3:26])[C:4](=[O:25])[C:5]1[CH:10]=[C:9]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[N:13]([CH3:31])[C:12]2=[O:22])[C:8]([F:23])=[CH:7][C:6]=1[Cl:24]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 10340Sodium CarbonateHCID 19832688HCID 19832688, compound

Product 1

HCID 19832668HCID 19832668, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 19.8 g of N-methoxy-N-methyl-2-chloro-5-[3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzamide, 5.7 ml of dimethyl sulphate as well as 14.0 g of sodium carbonate in 80 ml of acetonitrile is stirred at 50° C. for 1 hour. The mixture is then treated with 150 ml of ice-water and the aqueous mixture is extracted three times with 150 ml of ethyl acetate each time. The combined organic phases are washed to neutrality, dried over anhydrous sodium sulphate and the solvent is evaporated. The crude product is recrystallized from diethyl ether/n-hexane and gives N-methoxy-N-methyl-2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzamide, m.p. 158° C.

Workup

  1. extractionthe aqueous mixture is extracted three times with 150 ml of ethyl acetate each time
  2. washThe combined organic phases are washed to neutrality
  3. dry with materialdried over anhydrous sodium sulphate
  4. customthe solvent is evaporated
  5. customThe crude product is recrystallized from diethyl ether/n-hexane

Sources & evidence

ORD record
ord-ad1c499fc27d4f65be352f431a0280fb
Source dataset
uspto-grants-1991_05
Patent number
US05017211

Reaction notes

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