Hydrochloric Acid → HCID 54365318, compound

HRID 1706970Notes

Reaction equation

HRID 1706970 reaction equation
Cl.[Cl:2][C:3]1[CH:27]=[CH:26][CH:25]=[CH:24][C:4]=1[C:5]([C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[N:14]1[C:18]([CH2:19][Cl:20])=[N:17][C:16]([C:21]([OH:23])=[O:22])=[N:15]1)=[O:6].[CH3:28]O>>[CH3:28][O:22][C:21]([C:16]1[N:17]=[C:18]([CH2:19][Cl:20])[N:14]([C:8]2[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:7]=2[C:5](=[O:6])[C:4]2[CH:24]=[CH:25][CH:26]=[CH:27][C:3]=2[Cl:2])[N:15]=1)=[O:23]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887Methanol3×HCID 13255884HCID 13255884, compound

Product 1

HCID 54365318HCID 54365318, compound

Procedure

270 ml of a 6 N solution of hydrogen chloride in methanol is added to a solution of 133.0 g (0.30 mole) of 1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-(chloromethyl)-1H-1,2,4-triazole-3-carboxylic acid (crystals containing an equimolar amount of methanol; see German `Offenlegungschrift` No. 2,159,527, page 32) in 1400 ml of methanol, and the whole is refluxed for 18 hours. The reaction mixture is then concentrated in vacuo; water is added to the residue and extraction is performed twice with methylene chloride. The organic phase is washed once with saturated potassium bicarbonate solution, twice with water and once with saturated sodium chloride solution; it is subsequently dried over sodium sulphate and concentrated in vacuo. The residue is recrystallised from 1 liter of methanol. After drying there is obtained 1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-(chloromethyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester, m.p. 130°-132°.

Workup

  1. concentrationThe reaction mixture is then concentrated in vacuo
  2. additionwater is added to the residue and extraction
  3. washThe organic phase is washed once with saturated potassium bicarbonate solution, twice with water and once with saturated sodium chloride solution
  4. dry with materialit is subsequently dried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue is recrystallised from 1 liter of methanol
  7. customAfter drying there

Sources & evidence

ORD record
ord-4f14c93182bc4b598d78b36a18fe9870
Source dataset
uspto-grants-1980_06
Patent number
US04209515

Reaction notes

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