Water → (4-(3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethyl)-3,4-dichlorobenzoate

HRID 963047Notes

Reaction equation

HRID 963047 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:7]=1[N:13]1[C:17]([CH3:18])=[N:16][N:15]=[C:14]1[CH2:19][OH:20])=[O:5].C(N(CC)CC)C.[Cl:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][C:41]=1[Cl:42])[C:36](Cl)=[O:37].O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:7]=1[N:13]1[C:17]([CH3:18])=[N:16][N:15]=[C:14]1[CH2:19][O:20][C:36](=[O:37])[C:35]1[CH:39]=[CH:40][C:41]([Cl:42])=[C:33]([Cl:32])[CH:34]=1)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 190851734-(3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl)-3-hydroxymethyl-5-methyl[1,2,4]triazole

Product 1

HCID 19085140(4-(3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethyl)-3,4-dichlorobenzoateYield 68.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-(3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl)-3-hydroxymethyl-5-methyl[1,2,4]triazole (1.08 g) was dissolved in chloroform (50 ml). Triethylamine (0.34 g) and 3,4-dichlorobenzoyl chloride (0.69 g) were added, and the mixture was stirred at room temperature for 2 hours. Then, water was added to the solution for washing, and the mixture was dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (developing solvent:ethyl acetate-methanol) and recrystallized from ethyl acetate-diisopropyl ether to give 1.10 g of (4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethyl)-3,4-dichlorobenzoate.

Workup

  1. washfor washing
  2. dry with materialthe mixture was dried over magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography (developing solvent:ethyl acetate-methanol)
  5. customrecrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-c280b730bc7c424c959dd3b180727168
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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