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

HRID 1007572Notes

Reaction equation

HRID 1007572 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].[H][H].[CH3:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]=[C:24]=[O:25]>C(OC)(C)(C)C.[Pd]>[CH3:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][C:24](=[O:25])[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

6

Reactant 3

HCID 691942-Tolyl isocyanateHCID 6029613-Methoxy-4-nitrobenzyl alcoholHCID 178418361HCID 178418361, compound

Product 1

HCID 113920284-(3-(2-Methylphenyl)ureido)-3-methoxybenzyl alcohol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 15413tert-Butyl methyl etherSolvent

Procedure

15 g (81.8 mmol) of 3-methoxy-4-nitrobenzyl alcohol were hydrogenated in 500 mL of methyl tert-butyl ether over 1.3 g of palladium/carbon (10%; 50% water) while cooling in ice. After hydrogen uptake had ceased, the catalyst was filtered off, and 10.14 mL (81.8 mmol) of 2-methylphenyl isocyanate were added to the stirred filtrate over the course of 30 minutes. The reaction mixture was left to stand overnight, and the precipitated solid was filtered off with suction and washed with methyl tert-butyl ether. Yield: 20.5 g (88%).

Workup

  1. temperaturewhile cooling in ice
  2. filtrationthe catalyst was filtered off
  3. waitThe reaction mixture was left
  4. filtrationthe precipitated solid was filtered off with suction
  5. washwashed with methyl tert-butyl ether

Sources & evidence

ORD record
ord-9b2688b80cb84021924e2613d8875785
Source dataset
uspto-grants-2004_09
Patent number
US06794517B2

Reaction notes

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