m-Tolyl isocyanate → HCID 17283817, compound

HRID 239871Notes

Reaction equation

HRID 239871 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[N:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1)=[C:11]=[O:12]>ClCCl>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:11]([NH:10][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)=[O:12])=[C:4]([F:9])[CH:3]=1

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 1230504-Bromo-2-fluoroaniline

Product 1

HCID 17283817HCID 17283817, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 0° C. solution of 4-bromo-2-fluoroaniline (1 g, 5.26 mmol) in dichloromethane (10 mL) was treated dropwise with 1-isocyanato-3-methylbenzene (0.71 mL, 5.26 mmol), warmed to room temperature, stirred for 18 hours, and filtered. The filter cake was washed with dichloromethane and dried to provide 0.62 g of the desired product. MS (ESI(−)) m/e 321 (M−H)−.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with dichloromethane
  3. customdried

Sources & evidence

ORD record
ord-b60b94ea8c9846388995d14263405866
Source dataset
uspto-grants-2014_02
Patent number
US08642776B2

Reaction notes

Loading…