N-[4-Chloro-3-(trifluoromethyl)phenyl]-N′-[(3-nitrophenyl)methyl]urea → HCID 59708718, compound

HRID 1809157Notes

Reaction equation

HRID 1809157 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=2)=[O:10])=[CH:4][C:3]=1[C:22]([F:25])([F:24])[F:23]>CO>[NH2:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][NH:11][C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:22]([F:25])([F:23])[F:24])[CH:4]=1)=[O:10]

Participants

3

Reactant 1

HCID 59708553N-[4-Chloro-3-(trifluoromethyl)phenyl]-N′-[(3-nitrophenyl)methyl]urea

Product 1

HCID 59708718HCID 59708718, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a round bottom flask was added urea 26 (700 mg, 1.87 mmol, 1.0 eq.) and methanol (15 mL). The flask was then flushed with N2 before adding 10% Pd/C (35 mg, 5% by wt.). The reaction was placed under atmospheric H2 and allowed to stir at RT for 2 h before filtering over celite and rinsing with methanol. Concentration via rotary evaporation followed by column chromatography with silica gel and 1:1 EtOAc:Hexanes afforded pure urea 27 as a white solid (415 mg, 65% yield). LC/MSD (BP Series 1100 MSD) MS (ES+) m/z 344.1 (M+H)+1 1H-NMR, Varian 400 M DMSO-d6) δ 9.05 (br. s, 1H), 8.09 (d, 1H), 7.55 (m, 2H), 6.93 (t, 1H), 6.48 (s, 1H), 6.40 (d, 2H), 5.05 (s, 2H), 4.20 (s, 2H) ppm.

Workup

  1. customThe flask was then flushed with N2
  2. additionbefore adding 10% Pd/C (35 mg, 5% by wt.)
  3. filtrationbefore filtering over celite
  4. washrinsing with methanol
  5. concentrationConcentration
  6. customvia rotary evaporation

Sources & evidence

ORD record
ord-c51b37b763f743aa93502e5eccc81f19
Source dataset
uspto-grants-2013_01
Patent number
US08362017B2

Reaction notes

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