Methyl iodide → N-(2-methoxyethyl)-N-methyl-2-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)benzenesulfonamide

HRID 1110149Notes

Reaction equation

HRID 1110149 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][NH:7][S:8]([C:11]1[CH:16]=[C:15]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]([CH3:28])[C:18]2=[O:29])[CH:14]=[CH:13][C:12]=1[Cl:30])(=[O:10])=[O:9].Cl[C:32]1C=CC(N2C(=O)C=C(C(F)(F)F)N(C)C2=O)=CC=1S(Cl)(=O)=O.COCCN.IC>CN(C)C=O>[CH3:3][O:4][CH2:5][CH2:6][N:7]([CH3:32])[S:8]([C:11]1[CH:16]=[C:15]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:25])([F:27])[F:26])[N:19]([CH3:28])[C:18]2=[O:29])[CH:14]=[CH:13][C:12]=1[Cl:30])(=[O:10])=[O:9]

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 80182-MethoxyethylamineHCID 24758Sodium hydrideHCID 153348022-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)pyrimidinyl)benzenesulfonyl chlorideHCID 18993683N-(2-methoxyethyl)-2-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)benzenesulfonamide2×

Product 1

HCID 18993675N-(2-methoxyethyl)-N-methyl-2-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

To a stirred slurry of 0.2 g of a 60% dispersion of sodium hydride in mineral oil and 30 ml of N,N-dimethylformamide (DMF) cooled to 5° C. was added 1.95 g of N-(2-methoxyethyl)-2-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)benzenesulfonamide (Compound #52) prepared according to the procedure set forth above Process B using 2-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)pyrimidinyl)benzenesulfonyl chloride and 2-methoxyethylamine After stirring for 1 hour at 5° C. 0.6 ml of iodomethane was added to the reaction mixture. After stirring at room temperature for 16 hours, the mixture was concentrated using a rotary evaporator. The resulting gummy residue was treated several times with water until a solid had formed. The solid was recrystallized from ethanol to give 1.3 g of the title compound as a white crystalline solid, m.p. 108°-110° C. Spectral data for this compound is found in Table I.

Workup

  1. customprepared
  2. stirringAfter stirring at room temperature for 16 hours
  3. concentrationthe mixture was concentrated
  4. customa rotary evaporator
  5. additionThe resulting gummy residue was treated several times with water until a solid
  6. customhad formed
  7. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-ac9fa17118d14db8a13a17f0ed2f9259
Source dataset
uspto-grants-1994_06
Patent number
US05324854

Reaction notes

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