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

HRID 1062711Notes

Reaction equation

HRID 1062711 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/charcoal (10%; 50% water) while cooling with ice. After the uptake of hydrogen had ceased, the catalyst was filtered off and 10.14 mL (81.8 mmol) of 2-methylphenyl isocyanate were added to the filtrate within 30 minutes while stirring. 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 with 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-d5b1586c62d74d9e95070c4e7b5c9f55
Source dataset
uspto-grants-2005_11
Patent number
US06962937B2

Reaction notes

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