Dimethyl Sulfoxide → (1,2,4)Triazolo(1,5-a)pyrimidine-2-sulfonamide, N-(2,6-dichloro-3-methylphenyl)-5,7-dimethyl-

HRID 1165545Notes

Reaction equation

HRID 1165545 reaction equation
Cl[S:2]([C:5]1[N:15]=[C:8]2[N:9]=[C:10]([CH3:14])[CH:11]=[C:12]([CH3:13])[N:7]2[N:6]=1)(=[O:4])=[O:3].C[Si](C)(C)[NH:18][C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[C:21]([CH3:26])[C:20]=1[Cl:27].CS(C)=O>CC#N>[Cl:27][C:20]1[C:21]([CH3:26])=[CH:22][CH:23]=[C:24]([Cl:25])[C:19]=1[NH:18][S:2]([C:5]1[N:15]=[C:8]2[N:9]=[C:10]([CH3:14])[CH:11]=[C:12]([CH3:13])[N:7]2[N:6]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 6112325,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonyl chlorideHCID 11128643N-trimethylsilyl-2,6-dichloro-3-methylaniline

Product 1

HCID 14155157(1,2,4)Triazolo(1,5-a)pyrimidine-2-sulfonamide, N-(2,6-dichloro-3-methylphenyl)-5,7-dimethyl-Yield 81.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution consisting of 106.8 mg (0.433 mmole) of 2-chlorosulfonyl-5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine, 0.5 ml of CH3CN, and 252 μl (130 mmole) of N-trimethylsilyl-3-methyl-2,6-dichloroaniline was stirred at room temperature and 10 μl (0.14 mmole) of dimethyl sulfoxide (DMSO) added dropwise. The solution was stirred for 2 hours during which time a precipitate formed. The CH3CN was removed under nitrogen and the residual solid treated with 1 ml of 1N HCl. The mixture was stirred for 10 min, filtered, and the precipitate washed with acetone to obtain 136 mg of N-(2,6-dichloro-3-methylphenyl)-5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide product as an off-white solid. The solid was washed with methanol and dried to give 120 mg (0.310 mmole, 71.6 percent yield) of product as a white solid, m.p. 286.5°-288° C.

Workup

  1. stirringThe solution was stirred for 2 hours during which time a precipitate
  2. customformed
  3. customThe CH3CN was removed under nitrogen
  4. additionthe residual solid treated with 1 ml of 1N HCl
  5. stirringThe mixture was stirred for 10 min
  6. filtrationfiltered
  7. washthe precipitate washed with acetone

Sources & evidence

ORD record
ord-9345567360184fc2bf6b9aef98375708
Source dataset
uspto-grants-1990_03
Patent number
US04910306

Reaction notes

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