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

HRID 2251309Notes

Reaction equation

HRID 2251309 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-442fdc50fb264519892896a0f28a9c40
Source dataset
uspto-grants-2008_01
Patent number
US07319111B2

Reaction notes

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