Benzoyl isothiocyanate → 6-Thioureido-nicotinic acid ethyl ester

HRID 1985766Notes

Reaction equation

HRID 1985766 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[N:7][CH:6]=1)[CH3:2].C([N:21]=[C:22]=[S:23])(=O)C1C=CC=CC=1.[O-]CC.[Na+]>C1COCC1.C(O)C>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:22]([NH2:21])=[S:23])=[N:7][CH:6]=1)[CH3:2]

Participants

6

Reactant 3

HCID 68284Benzoyl isothiocyanateHCID 235927Ethyl 6-AminonicotinateHCID 2723922Sodium ethoxide

Product 1

HCID 220190876-Thioureido-nicotinic acid ethyl esterYield 77%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of ethyl-6-amino-nicotinate (2.5 g, 15 mmol) and benzoyl isothiocyanate (2.45 g, 15 mmol) in THF (20 mL) was heated at 40° C. for 4 h. To this mixture at RT, was added sodium ethoxide (2.04 g, 30 mmol) in ethanol (10 mL). After stirring the resulting mixture at RT for 16 h, the volatiles were removed in vacuo. The residue was suspended in aqueous NH4Cl and the solid formed was collected by filtration, rinsed with water and dried to afford 6-thioureido-nicotinic acid ethyl ester as a white solid (2.6 g, 77% yield). LC/MS; (M+H)+=226.

Workup

  1. customthe volatiles were removed in vacuo
  2. customthe solid formed
  3. filtrationwas collected by filtration
  4. washrinsed with water
  5. customdried

Sources & evidence

ORD record
ord-93eb81c6b7a541f8ac484d890aa60477
Source dataset
uspto-grants-2009_06
Patent number
US07547711B2

Reaction notes

Loading…