Water → HCID 20333039, compound

HRID 1706975Notes

Reaction equation

HRID 1706975 reaction equation
O.Cl.[OH:3][CH:4]([C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[N:18]1[C:22]([CH2:23][N:24]([CH3:26])[CH3:25])=[N:21][C:20]([C:27]([NH2:29])=[O:28])=[N:19]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>S(=O)(=O)(O)O.CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[ClH:17].[C:4]([C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[N:18]1[C:22]([CH2:23][N:24]([CH3:26])[CH3:25])=[N:21][C:20]([C:27]([NH2:29])=[O:28])=[N:19]1)(=[O:3])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 2

HCID 962WaterHCID 20333008HCID 20333008, compound

Product 1

HCID 20333039HCID 20333039, compound

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalyst2×HCID 180AcetoneSolventHCID 1118Sulfuric AcidSolvent

Procedure

2.50 ml (corresponding to 0.0067 mole of chromium trioxide) of an oxidation solution according to Jones (preparation of 250 ml by dissolving of 66.8 g of chromium trioxide in 57.5 ml of concentrated sulphuric acid and making up with water to 250 ml) is added dropwise at room temperature, with stirring, to a solution of 4.22 g (0.01 mole) of 1-[2-(α-hydroxybenzyl)-4-chlorophenyl]-5-[(dimethylamino)-methyl]-1H-1,2,4-triazole-3-carboxamide-hydrochloride in 800 ml of acetone. The reaction mixture, gradually assuming a green colour, is stirred for 18 hours at room temperature, and then concentrated in vacuo to 100 ml. Ice and saturated sodium carbonate solution are added until the pH-value has reached 10, and extraction is performed twice with ethyl acetate. The organic phase is washed twice with water and once with saturated sodium chloride solution and dried over magnesium sulphate. The drying agent is filtered off, and there is added to the filtrate ethereal hydrogen chloride solution until the pH-value has reached 3. The hydrochloride, precipitating in crystalline form, is filtered off with suction and washed with ethyl acetate and ether. After drying in vacuo, there is obtained 1-(2-benzoyl-4-chlorophenyl)-5-[(dimethylamino)-methyl]-1H-1,2,4-triazole-3-carboxamide-hydrochloride, m.p. 250° (with decomposition).

Workup

  1. custompreparation of 250 ml
  2. additionis added dropwise at room temperature
  3. concentrationconcentrated in vacuo to 100 ml
  4. additionIce and saturated sodium carbonate solution are added until the pH-value
  5. extraction10, and extraction
  6. washThe organic phase is washed twice with water and once with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulphate
  8. filtrationThe drying agent is filtered off
  9. additionthere is added to the filtrate ethereal hydrogen chloride solution until the pH-value
  10. customThe hydrochloride, precipitating in crystalline form
  11. filtrationis filtered off with suction
  12. washwashed with ethyl acetate and ether
  13. customAfter drying in vacuo

Sources & evidence

ORD record
ord-91ecfeeba1eb41d1ac4326d4f5fc1de0
Source dataset
uspto-grants-1980_06
Patent number
US04209515

Reaction notes

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