Water → HCID 18993681, compound

HRID 1110150Notes

Reaction equation

[H-].[Na+].[CH3:3][NH:4][S:5]([C:8]1[CH:13]=[C:12]([N:14]2C(=O)C=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]2=[O:26])[CH:11]=[CH:10][C:9]=1[Cl:27])(=[O:7])=[O:6].[C:28]1(S(Cl)(=O)=O)[CH:33]=CC=CC=1.CN.C(O[C:44](=[O:46])[CH3:45])(=O)C.[OH2:47]>CN(C=O)C>[C:33]([N:4]([CH3:3])[S:5]([C:8]1[CH:13]=[C:12]([N:14]2[C:44](=[O:46])[CH:45]=[C:17]([C:21]([F:22])([F:23])[F:24])[N:16]([CH3:25])[C:15]2=[O:26])[CH:11]=[CH:10][C:9]=1[Cl:27])(=[O:6])=[O:7])(=[O:47])[CH3:28]

Participants

Conditions

Temperature: 5 °C

Procedure

To a stirred mixture of 0.≠g of a 60% dispersion of sodium hydride in mineral oil and 30 ml of DMF cooled to 5° C. was added 1.5 g of N-methyl-2-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H) -pyrimidinyl)benzenesulfonamide. (Compound #40), prepared from 2-chloropyrimidinyl)benzenesulfonyl chloride and a 40% solution of methylamine in water following the procedure of Process B. After stirring for 1 hour at 5° C., 0.75 ml of acetic anhydride was added to the reaction mixture. After stirring at room temperature for 18 hours, the mixture was concentrated using a rotary evaporator. On treating the residue with cold water, 1.6 g of a brown solid was obtained. Further treatment of the solid with boiling ethanol and filtration gave 1.25 g of the title compound as an off-white solid, m.p. 193°-195° C. Spectral data for this compound is found in Table I.

Workup

stirringAfter stirring at room temperature for 18 hours
concentrationthe mixture was concentrated
customa rotary evaporator
additionOn treating the residue with cold water

Sources & evidence

ORD record: ord-d15b483b926a4bb286a7c84c6a8434a3
Source dataset: uspto-grants-1994_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05324854

Reaction notes

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