Ethyl isocyanate → HCID 59320850, compound

HRID 341188Notes

Reaction equation

HRID 341188 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[Br:6][C:7]1[CH:8]=[C:9]([NH2:13])[CH:10]=[N:11][CH:12]=1>COCCOC>[Br:6][C:7]1[CH:8]=[C:9]([NH:13][C:4]([NH:3][CH2:1][CH3:2])=[O:5])[CH:10]=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanate2×HCID 8176813-Amino-5-bromopyridine

Product 1

HCID 59320850HCID 59320850, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of EtNCO (1.6 ml, 20 mmol) and 5-bromo-pyridin-3-ylamine (1.73 g, 10 mmol) in DME (10 ml) was stirred and heated at 60° C. under N2. After 2 hours another aliquot of EtNCO (1.6 ml, 20 mmol) was added and the mixture was stirred at 60° C. for a further 16 hours. After cooling to RT the mixture was evaporated. The residue was triturated with EtOAc. The solid was collected by filtration and dried under vacuum to give the title compound (2.2 g) as a colourless solid. 1H NMR (400 MHz, DMSO-d6): 8.85 (1H, s), 8.43 (1H, d), 8.27 (1H, t), 8.21 (1H, d), 6.39 (1H, t), 3.19-3.05 (2H, m), 1.06 (3H, t).

Workup

  1. stirringthe mixture was stirred at 60° C. for a further 16 hours
  2. temperatureAfter cooling to RT the mixture
  3. customwas evaporated
  4. customThe residue was triturated with EtOAc
  5. filtrationThe solid was collected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-573c7199ad6d44c5afd326351f1ed38e
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

Loading…