p-Toluenesulfonic acid → HCID 21442753, compound

HRID 328612Notes

Reaction equation

HRID 328612 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:7]=1[N:13]=[N:14][CH:15]([NH:21][C:22](=O)[CH2:23][Cl:24])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][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:22]([CH2:23][Cl:24])=[N:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:14]1)=[O:5]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 53748705HCID 53748705, compound

Product 1

HCID 21442753HCID 21442753, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4.44 g. of ethyl [3-(2-chlorobenzoyl)-5-ethyl-2-thienyl]azochloroacetylaminoacetate, 1.90 g. of p-toluenesulfonic acid (monohydrate) and 80 ml. of benzene is refluxed for 40 minutes, then washed successively with an aqueous solution of sodium hydrogen carbonate and water, and dried over sodium sulfate. Thereafter, the solvent is evaporated to give ethyl 1-[3-(2-chlorobenzoyl)-5-ethyl-2-thienyl]-5-chloromethyl-1H-1,2,4-triazole-3-carboxylate as crystals. Recrystallization from ethanol yields pale yellow prisms melting at 114° to 115° C.

Workup

  1. additionA mixture of 4.44 g
  2. washwashed successively with an aqueous solution of sodium hydrogen carbonate and water
  3. dry with materialdried over sodium sulfate
  4. customThereafter, the solvent is evaporated

Sources & evidence

ORD record
ord-aa89eb56584141d4b636c0c9a3689c85
Source dataset
uspto-grants-1977_04
Patent number
US04017620

Reaction notes

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