Benzene, 1-isocyanato-2-methoxy- → 1-(2-Methoxyphenyl)-3-(2,4,6-trimethyl-3-pyrrolidin-1-yl-phenyl)-urea

HRID 2105274Notes

Reaction equation

HRID 2105274 reaction equation
[CH3:1][C:2]1[C:7]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[C:6]([CH3:13])[CH:5]=[C:4]([CH3:14])[C:3]=1[NH2:15].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]=[C:25]=[O:26]>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][C:25]([NH:15][C:3]1[C:4]([CH3:14])=[CH:5][C:6]([CH3:13])=[C:7]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[C:2]=1[CH3:1])=[O:26]

Participants

5

Reactant 2

HCID 69695Benzene, 1-isocyanato-2-methoxy-HCID 107982512,4,6-Trimethyl-3-(pyrrolidin-1-yl)aniline

Product 1

HCID 596436591-(2-Methoxyphenyl)-3-(2,4,6-trimethyl-3-pyrrolidin-1-yl-phenyl)-ureaYield 25.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2 (0.25 g, 1.22 mmol) and 2-methoxyphenyl isocyanate (0.18 g, 1.22 mmol) in toluene (5 mL) was heated at 80° C. overnight. The mixture was allowed to cool to room temperature and then diluted with EtOAc. The organic layer was washed with water (50 mL) and brine (50 mL) before it was dried (MgSO4) and concentrated on a rotavap. The residue was chromatographed on silica gel to give the title compound (0.11 g) as a solid. ESI [M+H+]=354.22.

Workup

  1. washThe organic layer was washed with water (50 mL) and brine (50 mL) before it
  2. dry with materialwas dried (MgSO4)
  3. concentrationconcentrated on a rotavap
  4. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-249f11c903ee45c2ac4663b92f662477
Source dataset
uspto-grants-2009_08
Patent number
US07579340B2

Reaction notes

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