Ammonia → HCID 20333039, compound

HRID 1706964Notes

Reaction equation

HRID 1706964 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:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:6]=1)=O.[NH3:29]>CO>[ClH:20].[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]([CH3:13])[CH3:12])=[N:9][C:5]([C:3]([NH2:29])=[O:2])=[N:6]1)(=[O:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 12831727HCID 12831727, compound

Product 1

HCID 20333039HCID 20333039, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

17.5 g (0.044 mole) of 1-(2-benzoyl-4-chlorophenyl)-5-[(dimethylamino)-methyl]-1H-1,2,4-triazole-3-carboxylic acid methyl ester (see Example 2) is covered over with 850 ml of methanol and 175 ml of concentrated aqueous ammonia solution. The reaction solution is stirred for 7 hours at room temperature, and afterwards 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 water and once with saturated sodium chloride solution; it is dried over sodium sulphate and concentrated in vacuo to dryness. The residue is dissolved in 300 ml of ethyl acetate, and ethereal hydrogen chloride solution is added until the pH-value has reached 2. The crystalline product is filtered with suction and washed with ethyl acetate and ether. After drying in vacuum, there is obtained 1-(2-benzoyl-4-chlorophenyl)-5-[(dimethylamino)-methyl]-1H-1,2,4-triazole-3-carboxamide-hydrochloride, m.p. 250°-255° with decomposition.

Workup

  1. concentrationafterwards concentrated in vacuo to dryness
  2. additionWater is added to the residue, and extraction
  3. washThe organic phase is washed twice with water and once with saturated sodium chloride solution
  4. dry with materialit is dried over sodium sulphate
  5. concentrationconcentrated in vacuo to dryness
  6. dissolutionThe residue is dissolved in 300 ml of ethyl acetate
  7. additionethereal hydrogen chloride solution is added until the pH-value
  8. filtrationThe crystalline product is filtered with suction
  9. washwashed with ethyl acetate and ether
  10. customAfter drying in vacuum

Sources & evidence

ORD record
ord-0a27e7e80d054019bde1171cd822f967
Source dataset
uspto-grants-1980_06
Patent number
US04209515

Reaction notes

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