4-Methylphenyl isocyanate → N-(2-methylcarbamoyl-5-tert-butyl-3-pyrrolyl)-N'-(4-methylphenyl)urea

HRID 1698918Notes

Reaction equation

HRID 1698918 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[NH:6][C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:8][C:9]=1[NH2:10])=[O:4].[C:15]1([CH3:24])[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[O:23])=[CH:17][CH:16]=1>C(Cl)Cl>[CH3:1][NH:2][C:3]([C:5]1[NH:6][C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:8][C:9]=1[NH:10][C:22]([NH:21][C:18]1[CH:19]=[CH:20][C:15]([CH3:24])=[CH:16][CH:17]=1)=[O:23])=[O:4]

Participants

4

Reactant 2

HCID 693254-Methylphenyl isocyanateHCID 183223852-(N-methylcarbamoyl)-3-amino-5-tert-butylpyrrole

Product 1

HCID 10268342N-(2-methylcarbamoyl-5-tert-butyl-3-pyrrolyl)-N'-(4-methylphenyl)ureaYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(N-methylcarbamoyl)-3-amino-5-tert-butylpyrrole (0.14 g, 0.70 mmol) in CH2Cl2 (5 mL) at room temp. was annd p-tolyl isocyanate (0.088 mL, 0.70 mmol, 1.0 equiv) and the resulting mixture was allowed to stir at room temp. overnight. The resulting precipitate was separated and washed with CH2Cl2 to give N-(2-methylcarbamoyl-5-tert-butyl-3-pyrrolyl)-N′-(4-methylphenyl)urea (0.17 g, 74%): mp 164-166° C.; 1H-NMR (DMSO-d6) δ1.23 (s, 9H), 2.19 (s, 3H), 2.75 (d, J=4.41 Hz, 3H), 6.49 (d, J=2.57 Hz, 1H), 7.01 (d, J=8.46 Hz, 2H), 7.33 (d, J=8.46 Hz, 2H), 7.60-7.63 (m, 1H), 9.45 (s, 1H), 9.50 (s, 1H), 10.17 (br s, 1H); FAB-LRMS m/z 329 (M+H).

Workup

  1. customat room temp.
  2. customThe resulting precipitate was separated
  3. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-53c2173835824803a0fcb169bc79f35e
Source dataset
uspto-grants-2002_02
Patent number
US06344476B1

Reaction notes

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