Phosphorus oxychloride → 5,7-dichloro-N-(2,6-dichloro-3-methylphenyl)-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide

HRID 1084972Notes

Reaction equation

HRID 1084972 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][S:11]([C:14]1[N:18]=[C:17]([NH2:19])[NH:16][N:15]=1)(=[O:13])=[O:12].[C:20]([Cl:26])(=O)[CH2:21][C:22]([Cl:24])=O.O=P(Cl)(Cl)Cl>C(#N)C>[Cl:24][C:22]1[CH:21]=[C:20]([Cl:26])[N:16]2[N:15]=[C:14]([S:11]([NH:10][C:3]3[C:4]([Cl:9])=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=3[Cl:1])(=[O:13])=[O:12])[N:18]=[C:17]2[N:19]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 74269Propanedioyl dichloride2×HCID 178425411HCID 178425411, compound

Product 1

HCID 150175485,7-dichloro-N-(2,6-dichloro-3-methylphenyl)-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamideYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 6.44 g (0.02 moles) of N-(3-(((2,6-dichloro-3-methylphenyl)amino)sulfonyl)-1H-1,2,4-triazol-5-yl)amine in 100 mL of dry acetonitrile was added 2.82 g (0.02 moles) of freshly distilled malonyl chloride. The mixture was stirred at room temperature overnight after which time some starting material remained. Additional malonyl chloride (0.56 g) was added and stirring was continued for 4 hrs. The reaction mixture was concentrated to dryness and the residue was slurried with POCl3 (122 g; 0.8 moles) and heated at 90° C. for 9 hrs. The reaction mixture was cooled and concentrated under reduced pressure and the residue was poured into ice-water. The resulting precipitate was filtered and dried to give 8.35 g of product having a purity of 75 percent (73 percent yield).

Workup

  1. stirringstirring
  2. waitwas continued for 4 hrs
  3. concentrationThe reaction mixture was concentrated to dryness
  4. temperatureheated at 90° C. for 9 hrs
  5. temperatureThe reaction mixture was cooled
  6. concentrationconcentrated under reduced pressure
  7. additionthe residue was poured into ice-water
  8. filtrationThe resulting precipitate was filtered
  9. customdried

Sources & evidence

ORD record
ord-b8af95582b8647348e441630e027ef3b
Source dataset
uspto-grants-1991_04
Patent number
US05006656

Reaction notes

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