4-(Isocyanatomethyl)-1,2-dimethoxybenzene → HCID 44128380, compound

HRID 2098292Notes

Reaction equation

HRID 2098292 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH2:6][N:7]=[C:8]=[O:9].[N+:15](=[C:17]1[N:21]=[CH:20][N:19]=[C:18]1[C:22]([NH2:24])=[O:23])=[N-:16]>CS(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH2:6][N:7]1[C:8](=[O:9])[N:21]2[CH:20]=[N:19][C:18]([C:22]([NH2:24])=[O:23])=[C:17]2[N:15]=[N:16]1

Participants

4

Reactant 2

HCID 242713714-(Isocyanatomethyl)-1,2-dimethoxybenzeneHCID 534265854-Diazo-4H-imidazole-5-carboxamide

Product 1

HCID 44128380HCID 44128380, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Crude 3,4-dimethoxybenzyl isocyanate (4 mmol) was added to a suspension of 5-diazoimidazole-4-carboxamide (0.274 g, 2 mmol) in dry dimethylsulfoxide (2.5 mL) at room temperature under nitrogen. The resulting mixture was stirred at room temperature overnight. The reaction was quenched by the addition of ice and the solid product was removed by filtration and purified by column chromatography to give the title compound as a white solid. Yield: 0.068 g, 10%. IR vmax/cm−1 1734, 1686, 1616. 1H NMR δH (DMSO-d6) 3.73 (3H, s, OMe), 3.74 (3H, s, OMe), 5.42 (2H, s, CH2Ar), 6.91-6.98 (2H, m, ArH), 7.03 (1H, d, J=1.9, ArH), 7.70 (1H, br s, NH), 7.82 (1H, br s, NH), 8.83 (1H, s, 6-H). δC (DMSO-d6) 52.2, 56.0, 56.0, 112.1, 112.4, 121.1, 128.3, 129.4, 131.3, 134.9, 139.6, 149.1, 149.2, 162.0.

Workup

  1. customThe reaction was quenched by the addition of ice
  2. customthe solid product was removed by filtration
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-094db4d20e9d45c8abab26aafc101605
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Reaction notes

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