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

HRID 1840615Notes

Reaction equation

HRID 1840615 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 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 over 1.3 g of palladium/carbon (10% strength; 50% water) in 500 mL of methyl tert-butyl ether with ice cooling. 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. Yield: 20.5 g (88%).

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-45de41897c1540068eafb31c8f8ea975
Source dataset
uspto-grants-2004_01
Patent number
US06680333B2

Reaction notes

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