HCID 21918625, compound → HCID 21918702, compound

HRID 987027Notes

Reaction equation

HRID 987027 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([NH:16][C:17]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=2)=[O:18])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3]>C(O)C.C(OCC)(=O)C.[Pd]>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][NH:19][C:17]([NH:16][C:7]2[CH:6]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:8]=2)=[O:18])=[CH:22][CH:23]=1

Participants

5

Reactant 1

HCID 21918625HCID 21918625, compound

Product 1

HCID 21918702HCID 21918702, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 23938PalladiumSolvent

Procedure

In a 100 ml autoclave, 0.55 g (1.38 mmole) of N-[3,5-bis-(1,1-dimethylethyl)-4-hydroxyphenyl]-N′-[(4-nitrophenyl)methyl]-urea is dissolved in a 2/1 mixture of ethanol and ethyl acetate, in the presence of 10% Pd/C. After hydrogenation for one and a half hours at 20° C., under 20 PSI, the mixture is filtered on celite and the filtrate is concentrated under vacuum. The evaporation residue is diluted in 20 ml of diethyl ether and the expected product crystallizes spontaneously. The crystals are filtered out and rinsed with 20 ml of diethyl ether. A white powder is obtained with a yield of 60% (0.31 g). Melting point: 194-195° C.

Workup

  1. waitAfter hydrogenation for one and a half hours at 20° C.
  2. filtrationunder 20 PSI, the mixture is filtered on celite
  3. concentrationthe filtrate is concentrated under vacuum
  4. additionThe evaporation residue is diluted in 20 ml of diethyl ether
  5. customthe expected product crystallizes spontaneously
  6. filtrationThe crystals are filtered out
  7. washrinsed with 20 ml of diethyl ether
  8. customA white powder is obtained with a yield of 60% (0.31 g)

Sources & evidence

ORD record
ord-3478b9ecad404c6f892775a71d74d08e
Source dataset
uspto-grants-2003_10
Patent number
US06630461B2

Reaction notes

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