Thiourea → Ethyl 5-[[(amino)(imino)methyl]thiomethyl]-1,3-dimethyl-1H-pyrazole-4-carboxylate

HRID 2309157Notes

Reaction equation

HRID 2309157 reaction equation
Cl[CH2:2][C:3]1[N:7]([CH3:8])[N:6]=[C:5]([CH3:9])[C:4]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[NH2:15][C:16]([NH2:18])=[S:17]>C(O)C>[NH2:18][C:16](=[NH:15])[S:17][CH2:2][C:3]1[N:7]([CH3:8])[N:6]=[C:5]([CH3:9])[C:4]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 13729351Ethyl 5-(chloromethyl)-1,3-dimethyl-1H-pyrazole-4-carboxylate

Product 1

HCID 13729352Ethyl 5-[[(amino)(imino)methyl]thiomethyl]-1,3-dimethyl-1H-pyrazole-4-carboxylateYield 126.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution under nitrogen was prepared from 10.7 g of the compound produced in Example 1 and 3.95 g of thiourea in 200 ml of ethanol. After refluxing the solution four hours, it was allowed to stir at room temperature overnight. The solvent was removed under reduced pressure. Then, the residue was triturated with hexane to give 16 g of solid (wet weight), m.p. 175°-180° C.

Workup

  1. temperatureAfter refluxing the solution four hours, it
  2. customThe solvent was removed under reduced pressure
  3. customThen, the residue was triturated with hexane

Sources & evidence

ORD record
ord-8191ab3a5ff14d5691f5f2b69f790fb2
Source dataset
uspto-grants-1987_09
Patent number
US04693743

Reaction notes

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