1-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-3-(4-hydroxymethyl-phenyl)urea → 1-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-3-(4-formyl-phenyl)-urea

HRID 499196Notes

Reaction equation

HRID 499196 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=2)=[O:13])[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([CH:21]=[O:22])=[CH:19][CH:20]=2)=[O:13])[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 594208851-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-3-(4-hydroxymethyl-phenyl)urea

Product 1

HCID 594208691-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-3-(4-formyl-phenyl)-ureaYield 69.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 518 mg (1.72 mmol) of 1-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-3-(4-hydroxymethyl-phenyl)-urea in methylene chloride (25 mL) is added 2.7 g of MnO2. The mixture is stirred at room temperature for 3 hours. Then the mixture is filtered over Celite® and evaporated to obtain 353 mg (1.2 mmol, 68%) of the title compound as a white solid. (ES+(m/z) 301 [M+H]).

Workup

  1. filtrationThen the mixture is filtered over Celite®
  2. customevaporated

Sources & evidence

ORD record
ord-f1937d4d521f4fde8e45b62013c2dec2
Source dataset
uspto-grants-2010_08
Patent number
US07767674B2

Reaction notes

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