HCID 54527485, compound → HCID 53739405, compound

HRID 2110088Notes

Reaction equation

HRID 2110088 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:25][CH3:26])=[C:9]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[N+:22]([O-])=O)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:25][CH3:26])=[C:9]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[NH2:22])=[O:13])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 54527485HCID 54527485, compound

Product 1

HCID 53739405HCID 53739405, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of N-(5-tert-butyl-2-methoxyphenyl)-N′-(2-nitro-4-methylphenyl)urea (prepared in a manner analogous to Method B1a; 4.0 g, 11.2 mmol) in EtOH (100 mL) was added to a slurry of 10% Pd/C (0.40 g) in EtOH (10 mL), and the resulting mixture was stirred under an atmosphere of H2 (balloon) at room temp. for 18 h. The mixture was filtered through a pad of Celite® and concentrated in vacuo to afford the desired product (3.42 g, 94%) as a powder: mp 165-166° C.; 1H-NMR (DMSO-d6) δ 1.30 (s, 9H), 2.26 (s, 3H), 3.50 (br s, 2H), 3.71 (s, 3H), 6.39 (br s, 1H), 6.62 (s, 1H), 6.73 (d, J=8.46 Hz, 1H), 6.99 (dd, J=2.21, 8.46 Hz, 1H), 7.05 (d, J=8.46 Hz, 1H), 7.29 (s, 1H), 8.22 (d, J=2.57 Hz, 1H); FAB-MS m/z 328 ((M+H)+). C3. General Method of Thiourea Formation by Reaction with a Thioisocyanate

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-11e0f4845ba047d0b6ce6c1753c83a6d
Source dataset
uspto-grants-2009_04
Patent number
US07517880B2

Reaction notes

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