Ammonia → 1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-[(dimethylamino)-methyl]-1H-1,2,4-triazole-3-carboxamide

HRID 1706973Notes

Reaction equation

HRID 1706973 reaction equation
C[O:2][C:3]([C:5]1[N:9]=[C:8]([CH2:10][N:11]([CH3:13])[CH3:12])[N:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[C:21](=[O:29])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[N:6]=1)=O.[NH3:30]>CO>[Cl:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:21]([C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[N:7]1[C:8]([CH2:10][N:11]([CH3:12])[CH3:13])=[N:9][C:5]([C:3]([NH2:30])=[O:2])=[N:6]1)=[O:29]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 53665129HCID 53665129, compound

Product 1

HCID 128317381-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-[(dimethylamino)-methyl]-1H-1,2,4-triazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8.66 g (0.020 mole) of 1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-[(dimethylamino)-methyl]-1H-1,2,4-triazole-3-carboxylic acid methyl ester is covered over with 400 ml of methanol and 80 ml of concentrated aqueous ammonia solution. The reaction solution is stirred for 16 hours at room temperature, and thereupon concentrated in vacuo to dryness. Water is added to the residue and extraction is performed twice with methylene chloride. The organic phase is washed twice with ice-cold 1 N sodium hydroxide solution and is then extracted twice with 2 N hydrochloric acid solution. To the aqueous acidified solutions there are added ice and sufficient 5 N sodium hydroxide solution to bring the pH-value to 10. The precipitated base is taken up in methylene chloride. The organic phase is washed twice with water and once with saturated sodium chloride solution; it is dried over sodium sulphate and concentrated by evaporation to dryness. The amorphous residue is triturated with ether, whereupon the reaction product precipitates in crystalline form. It is filtered off with suction and washed with ether. After drying, there is obtained 1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-[(dimethylamino)-methyl]-1H-1,2,4-triazole-3-carboxamide, m.p. 177°-180°.

Workup

  1. concentrationconcentrated in vacuo to dryness
  2. additionWater is added to the residue and extraction
  3. washThe organic phase is washed twice with ice-cold 1 N sodium hydroxide solution
  4. extractionis then extracted twice with 2 N hydrochloric acid solution
  5. additionare added ice and sufficient 5 N sodium hydroxide solution
  6. washThe organic phase is washed twice with water and once with saturated sodium chloride solution
  7. dry with materialit is dried over sodium sulphate
  8. concentrationconcentrated by evaporation to dryness
  9. customThe amorphous residue is triturated with ether, whereupon the reaction product
  10. customprecipitates in crystalline form
  11. filtrationIt is filtered off with suction
  12. washwashed with ether
  13. customAfter drying

Sources & evidence

ORD record
ord-9f39f475a1334c2b81b280f94daedd56
Source dataset
uspto-grants-1980_06
Patent number
US04209515

Reaction notes

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