Triethylamine → HCID 178492090, compound

HRID 1389496Notes

Reaction equation

HRID 1389496 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.[C:12]([N:20]=[C:21]=[S:22])(=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCl>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:20][C:21]([SH:22])=[N:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68284Benzoyl isothiocyanateHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 178492090HCID 178492090, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 17 parts of (4-methoxyphenyl)hydrazine hydrochloride, 16.3 parts of benzoyl isothiocyanate, 10 parts of N,N-diethylethanamine and 130 parts of dichloromethane is stirred for 1 hour at room temperature. The mixture is washed with water and the solvent is evaporated. Then there are added 4.5 parts of sodium hydroxide solution 50% and 80 parts of ethanol to the residue and the whole is stirred and refluxed for 30 minutes. The mixture is neutralized with concentrated hydrochloric acid and diluted with water. The precipitated product is filtered off and crystallized from 1-butanol, yielding 13 parts (46%) of 1-(4-methoxyphenyl)-5-phenyl-1H-1,2,4-triazole-3-thiol; mp. 260° C.

Workup

  1. washThe mixture is washed with water
  2. customthe solvent is evaporated
  3. additionThen there are added 4.5 parts of sodium hydroxide solution 50% and 80 parts of ethanol to the residue
  4. stirringthe whole is stirred
  5. temperaturerefluxed for 30 minutes
  6. additiondiluted with water
  7. filtrationThe precipitated product is filtered off
  8. customcrystallized from 1-butanol

Sources & evidence

ORD record
ord-ccc6b75c944d41d78d80be7d9ad31a02
Source dataset
uspto-grants-1981_01
Patent number
US04244964

Reaction notes

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