Hydrochloric Acid → Sulfentrazone

HRID 59628Notes

Reaction equation

HRID 59628 reaction equation
[NH2:1][C:2]1[C:3]([Cl:19])=[CH:4][C:5]([Cl:18])=[C:6]([N:8]2[C:12](=[O:13])[N:11]([CH:14]([F:16])[F:15])[C:10]([CH3:17])=[N:9]2)[CH:7]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].O.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:19][C:3]1[CH:4]=[C:5]([Cl:18])[C:6]([N:8]2[C:12](=[O:13])[N:11]([CH:14]([F:15])[F:16])[C:10]([CH3:17])=[N:9]2)=[CH:7][C:2]=1[NH:1][S:21]([CH3:20])(=[O:23])=[O:22]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 962WaterHCID 1140TolueneHCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 110559662-(5-Amino-2,4-dichlorophenyl)-4-(difluoromethyl)-2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-one

Product 1

HCID 86369Sulfentrazone

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

The solid 1-(5-amino-2,4-dichlorophenyl)-4,5-dihydro-4-difluoromethyl-3-methyl-1,2,4-triazol-5(1H)-one (1.0 equiv.) and 1.2 equiv of methanesulfonyl chloride was suspended in 20 equivalent of water and the reaction mixture chilled to 10 C. Vigorous stirring was commenced and 0.05 equiv of tetrabutylammonium bromide in 0.05 equiv of toluene was added. Using a pH meter, the pH of the suspension was brought to 7.8 by adding adequate quantity of 1 molar sodium carbonate aqueous solution and dynamically maintained for 1 hour. The suspension was much reduced but not eliminated. Concentrated hydrochloric acid was added slowly to bring the pH of the reaction to 2.0 Wherein a precipitate was formed. The precipitate was collected by filtration, washed with water and dried to give the N-[2,4-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl] phenyl]methanesulfonamide as a white solid (0.41 equiv and 91% purity).

Workup

  1. temperaturethe reaction mixture chilled to 10 C
  2. temperaturedynamically maintained for 1 hour
  3. customthe pH of the reaction to 2.0 Wherein a precipitate
  4. customwas formed
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-7f3a77659be346f980d09e4c1cbfc8db
Source dataset
uspto-grants-2016_09
Patent number
US09440932B2

Reaction notes

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