2-Tolyl isocyanate → 4-(3-(2-Methylphenyl)ureido)-3-methoxybenzyl alcohol

HRID 2185001Notes

Reaction equation

HRID 2185001 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N+:11]([O-])=O)[CH2:6][OH:7].[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]=[C:22]=[O:23]>C(OC)(C)(C)C.[Pd]>[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][C:22](=[O:23])[NH:11][C:10]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 691942-Tolyl isocyanateHCID 6029613-Methoxy-4-nitrobenzyl alcohol

Product 1

HCID 113920284-(3-(2-Methylphenyl)ureido)-3-methoxybenzyl alcoholYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 15413tert-Butyl methyl etherSolvent

Procedure

15 g (81.8 mmol) of 3-methoxy-4-nitrobenzyl alcohol were hydrogenated with ice cooling on 1.3 g of palladium/carbon (10% strength; 50% water) in 500 ml of methyl tert-butyl ether. After the absorption of hydrogen was complete, the catalyst was filtered off and 10.14 ml (81.8 mmol) of 2-methylphenyl isocyanate were added to the filtrate with stirring in the course of 30 minutes. The reaction mixture was allowed to stand overnight, and the precipitated solid was filtered off with suction and washed with methyl tert-butyl ether. 20.5 g (88%) of 4-(3-(2-methylphenyl)ureido)-3-methoxybenzyl alcohol were obtained.

Workup

  1. customAfter the absorption of hydrogen
  2. filtrationthe catalyst was filtered off
  3. waitto stand overnight
  4. filtrationthe precipitated solid was filtered off with suction
  5. washwashed with methyl tert-butyl ether

Sources & evidence

ORD record
ord-1f7862dc14be4533b60cb73a93930e2d
Source dataset
uspto-grants-2002_06
Patent number
US06399643B1

Reaction notes

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