4-Methylphenyl isocyanate → HCID 9843254, compound

HRID 2110080Notes

Reaction equation

HRID 2110080 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([N:7]=[C:8]=[O:9])=[CH:3][CH:2]=1.[CH3:11][O:12][C:13]1[CH:19]=[CH:18][C:17]([S:20]([C:23]([F:26])([F:25])[F:24])(=[O:22])=[O:21])=[CH:16][C:14]=1[NH2:15]>CCOC(C)=O>[CH3:11][O:12][C:13]1[CH:19]=[CH:18][C:17]([S:20]([C:23]([F:24])([F:25])[F:26])(=[O:21])=[O:22])=[CH:16][C:14]=1[NH:15][C:8]([NH:7][C:4]1[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=1)=[O:9]

Participants

4

Reactant 2

HCID 693254-Methylphenyl isocyanateHCID 8254572-methoxy-5-(trifluoromethane)sulfonylaniline

Product 1

HCID 9843254HCID 9843254, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

p-Tolyl isocyanate (0.19 mL, 1.55 mmol) was added to a solution of 2-methoxy-5-(trifluoromethanesulfonyl)aniline (0.330 g, 1.29 mmol) in EtOAc (5 mL), and the reaction mixture was stirred at room temp. for 18 h. The resulting precipitate was collected by filtration and washed with Et2O to give a white solid (0.28 g). This material was then purified by HPLC (C-18 column, 50% CH3CN/50% H2O) and the resulting solids were triturated with Et2O to provide the title compound (0.198 g): 1H-NMR (CDCl3) δ 7.08 (d, J=8.5 Hz, 2H), 7.33 (d, J=8.5 Hz, 2H), 7.40 (d, J=8.8 Hz, 1H), 7.71 (dd, J=2.6, 8.8 Hz, 1H), 8.66 (s, 1H), 8.90 (d, J=2.6 Hz, 1H), 9.36 (s, 1H); FAB-MS m/z 389 ((M+1)+). B1c. General Method for the Reaction of an Aryl Amine with an Aryl Isocyanate

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with Et2O

Sources & evidence

ORD record
ord-0c7f3161c89c4a0b8e20b05b7dac8bdc
Source dataset
uspto-grants-2009_04
Patent number
US07517880B2

Reaction notes

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