Hydrochloric Acid → HCID 19912199, compound

HRID 1090996Notes

Reaction equation

HRID 1090996 reaction equation
N[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.N([O-])=O.[Na+].[S:24](=[O:26])=[O:25].[ClH:27]>O.C(O)(=O)C.[Cu](Cl)Cl>[Cl:18][C:5]1[CH:4]=[C:3]([Cl:19])[C:2]([S:24]([Cl:27])(=[O:26])=[O:25])=[CH:7][C:6]=1[N:8]1[C:12](=[O:13])[N:11]([CH:14]([F:16])[F:15])[C:10]([CH3:17])=[N:9]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 110559662-(5-Amino-2,4-dichlorophenyl)-4-(difluoromethyl)-2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-oneHCID 23668193Sodium Nitrite

Product 1

HCID 19912199HCID 19912199, compound

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred mixture of 12.0 g (0.0388 mole) of 1-(5-amino-2,4-dichlorophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one in 50 mL of hydrochloric acid was cooled to 0° C. A solution of 2.79 g (0.0405 mole) of sodium nitrite in 20 mL of water was added while maintaining a reaction temperature of approximately 0° C. After complete addition, the reaction mixture was allowed to warm to room temperature and stir for 1.5 hours. This mixture was added slowly to a solution of 5.44 g (0.0405 mole) of copper (II) chloride in 15 mL of water and 50 mL of acetic acid which was saturated with sulfur dioxide. The resultant mixture was stirred at room temperature for one hour, forming a precipitate. The reaction mixture was poured into ice water and was stirred for a brief period of time. This mixture was filtered to collect approximately 16 grams of 1-(2,4-dichloro-5-chlorosulfonylphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl -1,2,4-triazol-5(1H)-one as an off-white solid.

Workup

  1. temperaturewhile maintaining a reaction temperature of approximately 0° C
  2. additionAfter complete addition
  3. temperatureto warm to room temperature
  4. customforming a precipitate
  5. stirringwas stirred for a brief period of time
  6. filtrationThis mixture was filtered
  7. customto collect approximately 16 grams of 1-(2,4-dichloro-5-chlorosulfonylphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl -1,2,4-triazol-5(1H)-one as an off-white solid

Sources & evidence

ORD record
ord-d84e6b0d411449a5a1250eec382dc7fb
Source dataset
uspto-grants-1992_01
Patent number
US05084085

Reaction notes

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