4-Methylphenyl isocyanate → HCID 9884589, compound

HRID 1698894Notes

Reaction equation

HRID 1698894 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[S:6][C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:8][C:9]=1[NH2:10])=[O:4].[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]=[O:24])=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH3:1][NH:2][C:3]([C:5]1[S:6][C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:8][C:9]=1[NH:10][C:23]([NH:22][C:19]1[CH:20]=[CH:21][C:16]([CH3:15])=[CH:17][CH:18]=1)=[O:24])=[O:4]

Participants

4

Reactant 2

HCID 693254-Methylphenyl isocyanateHCID 18322369HCID 18322369, compound

Product 1

HCID 9884589HCID 9884589, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of the N-methyl-3-amino-5-tert-butylthiophene-2-carboxamide (0.60 g, 2.83 mmol) and 4-methylphenyl isocyanate (0.36 mL, 2.83 mmol) in toluene (2 mL) was heated at the reflux temp. for 18 h. The resulting solution was concentrated under reduced pressure and the resulting solid was purified by flash chromatography (EtOAc/CH2Cl2) affording N-(2-methylcarbamoyl-5-tert-butyl-3-thienyl)-N′-(4-methylphenyl)urea (0.42 g, 44%): mp 202-4° C.; 1H NMR (CDCl3) δ1.38 (s, 9H), 2.31 (s, 3H), 2.91 (d, J=4.9 Hz, 3H), 5.59 (bs, 1H), 7.11 (d, J=8.5 Hz, 2H), 7.29 (d, J=8.5 Hz, 2H), 7.90 (s, 1H), 10.53 (s, 1H).

Workup

  1. concentrationThe resulting solution was concentrated under reduced pressure
  2. customthe resulting solid was purified by flash chromatography (EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-ac3be2d73ddf4aac8b4036fd6e223a57
Source dataset
uspto-grants-2002_02
Patent number
US06344476B1

Reaction notes

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