Methyl iodide → HCID 18993685, compound

HRID 1110151Notes

Reaction equation

HRID 1110151 reaction equation
[CH3:1][N:2]([CH2:26][CH:27]=[CH2:28])[S:3]([C:6]1[CH:11]=[C:10]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]2=[O:24])[CH:9]=[CH:8][C:7]=1[Cl:25])(=[O:5])=[O:4].IC.[H][H]>[Pd].C(OCC)(=O)C>[CH3:1][N:2]([CH2:26][CH2:27][CH3:28])[S:3]([C:6]1[CH:11]=[C:10]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:21])([F:22])[F:20])[N:14]([CH3:23])[C:13]2=[O:24])[CH:9]=[CH:8][C:7]=1[Cl:25])(=[O:4])=[O:5]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 18993679HCID 18993679, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 18993685HCID 18993685, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.6 g of N-methyl-N-(2-propenyl)-2-chloro -5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)benzenesulfonamide (Compound #29), prepared by process C from Compound #28 and iodomethane, 100 ml of ethyl acetate and 200 mg of 5% palladium/carbon catalyst was hydrogenated in a Paar® apparatus at 28 psi of hydrogen. After 30 minutes, the catalyst was filtered and solvent removed from the filtrate by rotary evaporation. The glassy residue was treated with ethanol to give 1.4 g of the title compound as a light gray powder, m.p. 143.5°-145° C.

Workup

  1. filtrationthe catalyst was filtered
  2. customsolvent removed from the filtrate by rotary evaporation
  3. additionThe glassy residue was treated with ethanol

Sources & evidence

ORD record
ord-92a582b56b5c4d19a3fb8f9087512fa3
Source dataset
uspto-grants-1994_06
Patent number
US05324854

Reaction notes

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