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

HRID 1585089Notes

Reaction equation

HRID 1585089 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, then the resulting crystalline precipitate was collected by filtration, followed by recrystallization 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
  4. customfollowed by recrystallization from isopropyl ether

Sources & evidence

ORD record
ord-b03bb44677a84db58396e55570c0c0d8
Source dataset
uspto-grants-1999_08
Patent number
US05935963

Reaction notes

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