4-Methylphenyl isocyanate → HCID 9907392, compound

HRID 2110081Notes

Reaction equation

HRID 2110081 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]([CH:23]([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]([CH:23]([F:24])[F:25])(=[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 3374971HCID 3374971, compound

Product 1

HCID 9907392HCID 9907392, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

p-Tolyl isocyanate (0.058 mL, 0.46 mmol) was added to a solution of 2-methoxy-5-(difluoromethanesulfonyl)aniline (0.100 g, 0.42 mmol) in EtOAc (0.5 mL) and the reaction mixture was stirred at room temp. for 3 d. The resulting precipitate was filtered and washed with Et2O to provide the title compound as a white solid (0.092 g): 1H-NMR (CDCl3) δ 2.22 (s, 3H), 4.01 (s, 3H), 7.01-7.36 (m, 6H), 7.54 (dd, J=2.4, 8.6 Hz, 1H), 8.57 (s, 1H), 8.79 (d, J=2.6 Hz, 1H), 9.33 (s, 1H); EI-MS m/z 370 (M+). B1d. General Method for the Reaction of an Aryl Amine with an Aryl Isocyanate

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with Et2O

Sources & evidence

ORD record
ord-d3363f8a2dbe49eaa36281315aca8a7f
Source dataset
uspto-grants-2009_04
Patent number
US07517880B2

Reaction notes

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