Hydrochloric Acid → Sulfentrazone

HRID 59627Notes

Reaction equation

HRID 59627 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.O.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:34][S:35](Cl)(=[O:37])=[O:36].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:35]([CH3:34])(=[O:37])=[O:36]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 962WaterHCID 1140TolueneHCID 10340Sodium Carbonate2×HCID 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.) 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 of the suspension was brought to 7.8 by adding adequate quantity of 1 molar sodium carbonate aqueous solution. Simultaneous addition of 1.2 equiv methanesulfonyl chloride was started into the reaction while keeping the flow of the aqueous sodium carbonate on such that the pH of 7.8 was maintained throughout. After 45 minutes the reaction was complete and the suspension was replaced by a clear solution. 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 (0.96 equiv and 96% purity).

Workup

  1. temperaturethe reaction mixture chilled to 10 C
  2. customwas started into the reaction
  3. temperaturewas maintained throughout
  4. customthe pH of the reaction to 2.0 wherein a precipitate
  5. customwas formed
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-3a09bb510bc34a159a754319a649b5f6
Source dataset
uspto-grants-2016_09
Patent number
US09440932B2

Reaction notes

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