Dichloromethane → HCID 57265543, compound

HRID 1681101Notes

Reaction equation

HRID 1681101 reaction equation
[F:1][C:2]1[CH:7]=[C:6](F)[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](Cl)(=[O:24])=[O:23].C(Cl)Cl>O>[CH3:5][N:9]([CH3:10])[S:22]([C:3]1[CH:4]=[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[N:11]([CH3:20])[C:10]2=[O:21])[C:6]([N:11]([CH3:20])[CH3:12])=[CH:7][C:2]=1[F:1])(=[O:23])=[O:24]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 15334805HCID 15334805, compound

Product 1

HCID 57265543HCID 57265543, compoundYield 129.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.0 g of 2,4,-difluoro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H) pyrimidinyl)benzenesulfonyl chloride and 30 ml of methylene chloride cooled to 5° C. was added 1.9 ml of a 40% solution of dimethylaminein water over 15 minutes. Analysis of the reaction mixture by TLC after 2 hours of stirring showed a single component. Work up was carried out as described in Example B-4. Two grams of crude solid was obtained and recrystallized from ethanol giving 1.7 g of a white solid, melting point 185°-194° C. NMR analysis of the product showed a 2:1 mixture of N,N-dimethyl-2,4-difluoro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)benzenesulfonamide (Compound #49) and the title compound. A mixture of 1.6 g of the product, 30 ml of methylene chloride and 3.8 ml of a 40% solution of dimethylamine in water was stirred at roomtemperature for 21 hours. The organic layer was separated, washed with water and dried over magnesium sulfate. After removal of volatiles using arotary evaporator there remained 1.6 g of a solid. Recrystallization of theproduct from ethanol gave 1.4 g of the title compound as fine white crystals, m.p. 223.5°-225° C. Spectral data for this compound is found in Table I.

Workup

  1. customTwo grams of crude solid was obtained
  2. customrecrystallized from ethanol giving 1.7 g of a white solid, melting point 185°-194° C
  3. additiona 2:1 mixture of N,N-dimethyl-2,4-difluoro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)benzenesulfonamide (Compound #49)
  4. additionA mixture of 1.6 g of the product, 30 ml of methylene chloride and 3.8 ml of a 40% solution of dimethylamine in water
  5. stirringwas stirred at roomtemperature for 21 hours
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. customAfter removal of volatiles
  10. customevaporator there remained 1.6 g of a solid
  11. customRecrystallization of theproduct from ethanol

Sources & evidence

ORD record
ord-42fecd766ace44b9b73540033a752383
Source dataset
uspto-grants-1992_12
Patent number
US05169430

Reaction notes

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