Ethyl isothiocyanatoformate → N-(4-t-butoxycarbonylphenyl)-N'-ethoxycarbonyl thiourea

HRID 1417188Notes

Reaction equation

HRID 1417188 reaction equation
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:15]([O:17][C:18]([N:20]=[C:21]=[S:22])=[O:19])[CH3:16]>C(OC(C)C)(C)C>[C:1]([O:5][C:6]([C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:21]([NH:20][C:18]([O:17][CH2:15][CH3:16])=[O:19])=[S:22])=[CH:11][CH:12]=1)=[O:14])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl ester

Product 1

HCID 19361546N-(4-t-butoxycarbonylphenyl)-N'-ethoxycarbonyl thioureaYield 96.3%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

In 150 ml of isopropyl ether was dissolved 13.51 g of 4-amino-benzoic acid t-butyl ester. To the solution was added, while stirring at room temperature, 9.83 g of ethoxycarbonyl isothiocyanate. The mixture was stirred for two hours, the resulting crystalline precipitate was collected by filtration and recrystallizated from isopropyl ether to give 21.83 g of the title compound as colorless needles.

Workup

  1. additionTo the solution was added
  2. stirringThe mixture was stirred for two hours
  3. filtrationthe resulting crystalline precipitate was collected by filtration

Sources & evidence

ORD record
ord-9cc878eca2004d00a71da73c3fb07d30
Source dataset
uspto-grants-1999_03
Patent number
US05876756

Reaction notes

Loading…