Hydrochloric Acid → Flumetsulam

HRID 1165547Notes

Reaction equation

HRID 1165547 reaction equation
Cl[S:2]([C:5]1[N:14]=[C:8]2[N:9]=[C:10]([CH3:13])[CH:11]=[CH:12][N:7]2[N:6]=1)(=[O:4])=[O:3].C[Si](C)(C)[NH:17][C:18]1[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=1[F:25].CS(C)=O.Cl>CC#N>[F:24][C:23]1[CH:22]=[CH:21][CH:20]=[C:19]([F:25])[C:18]=1[NH:17][S:2]([C:5]1[N:14]=[C:8]2[N:9]=[C:10]([CH3:13])[CH:11]=[CH:12][N:7]2[N:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 141551085-Methyl[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonyl chlorideHCID 14626581HCID 14626581, compound

Product 1

HCID 91759FlumetsulamYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution consisting of 91.4 mg of about 77 percent pure 2-chlorosulfonyl-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine (0.30 mmole), 0.5 ml of CH3CN, 0.5 ml of N-trimethylsilyl-2,6-difluoroaniline, and 10 μl (0.141 mmole) of dimethyl sulfoxide was stirred at room temperature for 4 hours. The solution was treated with 2 ml of 1.0N HCl and the resultant mixture filtered. The precipitate was dried in vacuo, washed with CH2Cl2 and again dried to afford 68.7 mg (0.211 mmole, 70.0 percent yield) of N-(2,6-difluorophenyl)-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide product as a white powder, m.p. 250°-251° C.

Workup

  1. filtrationthe resultant mixture filtered
  2. customThe precipitate was dried in vacuo
  3. washwashed with CH2Cl2
  4. customagain dried

Sources & evidence

ORD record
ord-8bac7618e2b34489b2ee95b44e9cb76b
Source dataset
uspto-grants-1990_03
Patent number
US04910306

Reaction notes

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