N-(2-(2,5-Dimethyl-1-pyrrolyl)ethyl)-N'-(4-ethoxycarbonylphenyl)-thiourea → N-(2-(2,5-Dimethyl-1-pyrrolyl)ethyl)-N'-(4-carboxyphenyl)thiourea

HRID 1904222Notes

Reaction equation

HRID 1904222 reaction equation
[CH3:1][C:2]1[N:3]([CH2:8][CH2:9][NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:22]CC)=[O:21])=[CH:16][CH:15]=2)=[S:12])[C:4]([CH3:7])=[CH:5][CH:6]=1>[OH-].[Na+]>[CH3:7][C:4]1[N:3]([CH2:8][CH2:9][NH:10][C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]([OH:22])=[O:21])=[CH:18][CH:19]=2)=[S:12])[C:2]([CH3:1])=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 13770053N-(2-(2,5-Dimethyl-1-pyrrolyl)ethyl)-N'-(4-ethoxycarbonylphenyl)-thiourea

Product 1

HCID 13770054N-(2-(2,5-Dimethyl-1-pyrrolyl)ethyl)-N'-(4-carboxyphenyl)thiourea

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2.8 g (0.008 mol) of N-(2-(2,5-dimethyl-1-pyrolyl)ethyl)-N'-(4-ethoxycarbonylphenyl)thiourea, prepared as in Example 9, are stirred with 10 ml of 1 N sodium hydroxide solution at room temperature for 5 h and under reflux for 15 min. After cooling, the mixture is filtered, and the filtrate is acidified and the product is filtered off with suction. yield: 1.9 g (75% of theory), Melting point: 174°-175° C. Elemental analysis: C16H19N3O2S (317.41) calculated C 60.5 H 6.0 N 13.2 0 10.1 S 10.1 found: C 59.9 H 5.9 N 13.6 0 10.7 S 9.9

Workup

  1. temperatureunder reflux for 15 min
  2. temperatureAfter cooling
  3. filtrationthe mixture is filtered
  4. filtrationthe product is filtered off with suction

Sources & evidence

ORD record
ord-d5b389ab19664a1398081599bb3b228a
Source dataset
uspto-grants-1989_06
Patent number
US04837225

Reaction notes

Loading…