Sulfuric Acid → HCID 23035208, compound

HRID 35556Notes

Reaction equation

HRID 35556 reaction equation
S(=O)(=O)(O)[OH:2].[Cl:6][C:7]1[CH:12]=[C:11]([N:13]2[C:18](=[O:19])[NH:17][C:16](=[O:20])[CH:15]=[N:14]2)[CH:10]=[CH:9][C:8]=1[CH:21]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:22]#[N:23]>O>[Cl:6][C:7]1[CH:12]=[C:11]([N:13]2[C:18](=[O:19])[NH:17][C:16](=[O:20])[CH:15]=[N:14]2)[CH:10]=[CH:9][C:8]=1[CH:21]([C:24]1[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=1)[C:22]([NH2:23])=[O:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 58901Clazuril

Product 1

HCID 23035208HCID 23035208, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 30 parts of a sulfuric acid solution in water (90:10 by volume) were added portionwise during a period of 5 minutes 2 parts of 2-chloro-α-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)benzeneacetonitrile at room temperature. Upon completion, stirring was continued for 2 hours at 80° C. The reaction mixture was poured into ice water. The product was filtered off, washed with water and purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated in vacuo. The residue was stirred in 2,2'-oxybispropane. The product was filtered off and dried, yielding 1.1 parts (54%) of 2-chloro-α-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-benzeneacetamide; mp. 160.7° C. (intermediate 26).

Workup

  1. filtrationThe product was filtered off
  2. washwashed with water
  3. custompurified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated in vacuo
  7. stirringThe residue was stirred in 2,2'-oxybispropane
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-cf80aedb122541a8bdb94ad8dc0a1c79
Source dataset
uspto-grants-1988_08
Patent number
US04767760

Reaction notes

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