Nitrobenzene → HCID 178434201, compound

HRID 719276Notes

Reaction equation

HRID 719276 reaction equation
[CH3:1][C:2]1[C:6]([NH:7][C:8](=O)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:4][N:3]=1.[N+](C1C=CC=CC=1)([O-])=O.Cl[Sn](Cl)(Cl)Cl>O=P(Cl)(Cl)Cl>[CH3:1][C:2]1[C:6]2[N:7]=[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[C:5]=2[NH:4][N:3]=1

Participants

5

Reactant 3

HCID 7416NitrobenzeneHCID 24287Tin tetrachlorideHCID 178434571HCID 178434571, compound

Product 1

HCID 178434201HCID 178434201, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
185 °C

Procedure

To a mixture of 565 mg of N-(3-Methyl-5-phenyl-1H-pyrazol-4-yl)-benzamide was added 5 mL of nitrobenzene followed by 270 μL of POCl3 and the resulting mixture was heated at 185° C. After 1 h, 0.4 mL of a SnCl4 solution (1.0 M solution in heptane) was added and the mixture was heated for an additional 2 h, then concentrated under reduced pressure and purified by means of MPLC (12 g SiO2, 35% ethyl acetate:heptane) to give the title compound as a tan solid.

Workup

  1. temperaturethe mixture was heated for an additional 2 h
  2. concentrationconcentrated under reduced pressure
  3. custompurified by means of MPLC (12 g SiO2, 35% ethyl acetate:heptane)

Sources & evidence

ORD record
ord-5da67d4f1c7c4ed0b29c99be41e33210
Source dataset
uspto-grants-2006_11
Patent number
US07132428B2

Reaction notes

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