N-Methylisopropylamine → 3-[4-Chloro-2-fluoro-5-{[isopropyl(methyl)amino]carbonylaminosulfonyl}phenyl]-1-methyl-2,4-dioxo-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

HRID 18678

Reaction equation

HRID 18678 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[S:22]([N:25]=[C:26]=[O:27])(=[O:24])=[O:23].[CH3:28][NH:29][CH:30]([CH3:32])[CH3:31]>ClCCCl>[Cl:1][C:2]1[C:3]([S:22]([NH:25][C:26]([N:29]([CH:30]([CH3:32])[CH3:31])[CH3:28])=[O:27])(=[O:24])=[O:23])=[CH:4][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:17])[F:18])[N:11]([CH3:20])[C:10]2=[O:21])=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 78485N-MethylisopropylamineHCID 587094392-Chloro-4-fluoro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]benzenesulfonylisocyanate

Product 1

HCID 587094373-[4-Chloro-2-fluoro-5-{[isopropyl(methyl)amino]carbonylaminosulfonyl}phenyl]-1-methyl-2,4-dioxo-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

With stirring, 1.0 g (2.34 mmol) of 2-chloro-4-fluoro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]benzenesulfonyl isocyanate in 1,2-dichloroethane was added to a solution of 0.34 g (4.68 mmol) of N-methylisopropylamine in 1,2-dichloroethane, and the mixture was stirred overnight. The reaction mixture was concentrated, the residue was taken up in methylene chloride and 0.5N hydrochloric acid was added. The organic phase was then dried and the solvent was removed. This gave 0.5 g (42% of theory) of the title compound as a colorless solid (m.p.: 145° C.).

Workup

  1. stirringthe mixture was stirred overnight
  2. concentrationThe reaction mixture was concentrated
  3. addition0.5N hydrochloric acid was added
  4. customThe organic phase was then dried
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-dfb6cfc1a7aa40f98611b46339d471c2
Source dataset
uspto-grants-2010_06
Patent number
US07741485B2

Linked notes

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