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Hydrochloric Acid → Sulfentrazone

HRID 59630
Notes
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Reaction equation

HRID 59630 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(C)=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:35][S:36](Cl)(=[O:38])=[O:37].C(=O)([O-])[O-].[K+].[K+].Cl>[Cl-].C([N+](CCC)(CCC)CCC)CC>[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:36]([CH3:35])(=[O:38])=[O:37]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 962WaterHCID 7237O-XyleneHCID 10340Sodium CarbonateHCID 11430Potassium 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 79880Tetrapropylammonium chlorideCatalyst

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 tetra-n-propylammonium chloride in 0.05 equiv of xylene 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 potassium carbonate on such that the 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 (0.95 equiv and 97% 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-717c81d09fca4752a9bcc24f39afa373
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09440932B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes