4-Methylphenyl isocyanate → HCID 54563615, compound

HRID 2110079Notes

Reaction equation

HRID 2110079 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:12][CH:13]2[CH2:17][CH2:16][O:15][CH2:14]2)=[C:9]([CH:11]=1)[NH2:10])([CH3:4])([CH3:3])[CH3:2].[C:18]1([CH3:27])[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[O:26])=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:12][CH:13]2[CH2:17][CH2:16][O:15][CH2:14]2)=[C:9]([NH:10][C:25]([NH:24][C:21]2[CH:22]=[CH:23][C:18]([CH3:27])=[CH:19][CH:20]=2)=[O:26])[CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 693254-Methylphenyl isocyanateHCID 54390342HCID 54390342, compound

Product 1

HCID 54563615HCID 54563615, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5-tert-butyl-2-(3-tetrahydrofuranyloxy)aniline (0.078 g, 0.33 mmol) in toluene (2.0 mL) was added p-tolyl isocyanate (0.048 g, 0.36 mmol) and the resulting mixture was allowed to stir at room temp. for 8 h to produce a precipitate. The reaction mixture was filtered and the residue was sequentially washed with toluene and hexanes to give the desired urea as a white solid (0.091 g, 75%): mp 229-231° C.; 1H-NMR (DMSO-d6) δ 1.30 (s, 9H), 1.99-2.03 (m, 1H), 2.19-2.23 (m, 4H), 3.69-3.76 (m, 1H), 3.86-3.93 (m, 3H), 4.98-5.01 (m, 1H), 6.81-6.90 (m, 2H), 7.06 (d, J=8.09 Hz, 2H, 7.32 (d, J=8.09 Hz, 2H), 7.84 (s, 1H), 8.22 (d, J=2.21 Hz, 1H), 9.26 (s, 1H). B1b. General Method for the Reaction of an Aryl Amine with an Aryl Isocyanate

Workup

  1. customto produce a precipitate
  2. filtrationThe reaction mixture was filtered
  3. washthe residue was sequentially washed with toluene and hexanes

Sources & evidence

ORD record
ord-e170616e38994b4c99df1f55a8eeb3d3
Source dataset
uspto-grants-2009_04
Patent number
US07517880B2

Reaction notes

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