4-Methylphenyl isocyanate → HCID 23023097, compound

HRID 2110082Notes

Reaction equation

HRID 2110082 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]=[C:18]([O:20][CH3:21])[C:17]([C:22]([F:25])([F:24])[F:23])=[CH:16][C:14]=1[NH2:15]>CCOC(C)=O>[CH3:11][O:12][C:13]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([C:22]([F:24])([F:23])[F:25])=[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 27800032,4-dimethoxy-5-(trifluoromethyl)aniline

Product 1

HCID 23023097HCID 23023097, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

p-Tolyl isocyanate (0.16 mL, 1.24 mmol) was added to a solution of 2,4-dimethoxy-5-(trifluoromethyl)aniline (0.25 g, 1.13 mmol) in EtOAc (3 mL) and the resulting mixture was stirred at room temp. for 18 h. The resulting precipitate was washed with Et2O to give the title compound as a white solid (0.36 g): 1H-NMR (CDCl3) δ 2.21 (s, 3H), 3.97 (s, 3H), 3.86 (s, 3H), 6.88 (s, 1H), 7.05 (d, J=8.5 Hz, 2H), 7.29 (d, J=8.5 Hz, 2H), 8.13 (s, 1H), 8.33 (s, 1H), 9.09 (s, 1H); FAB-MS m/z 355 ((M+1)+). B1e. General Method for the Reaction of an Aryl Amine with an Aryl Isocyanate

Workup

  1. washThe resulting precipitate was washed with Et2O

Sources & evidence

ORD record
ord-5db46d012927401393f118a0eb664905
Source dataset
uspto-grants-2009_04
Patent number
US07517880B2

Reaction notes

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