p-Fluoronitrobenzene → HCID 14121576, compound

HRID 2352009Notes

Reaction equation

HRID 2352009 reaction equation
[C:1]([NH:9][CH2:10][CH2:11][OH:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[N+:15]([C:18]1[CH:23]=[CH:22][C:21](F)=[CH:20][CH:19]=1)([O-:17])=[O:16].[N+](C1C=CC=CC=1F)([O-])=O>ClC1C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([O:12][CH2:11][CH2:10][NH:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

8

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 14798Sodium HydroxideHCID 738951-Fluoro-2-nitrobenzeneHCID 5695262-Benzamidoethanol

Product 1

HCID 14121576HCID 14121576, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 7964ChlorobenzeneSolvent2×

Procedure

20.0 g of 2-benzoylaminoethanol are suspended in 60 ml of chlorobenzene. To the suspension are added 9.7 g of 50% strength sodium hydroxide solution and stirred in for some time until a homogeneous syrup has formed. 1.5 g of tetrabutylammonium bromide are then added, followed dropwise in the course of 15 minutes by 14.3 g of 4-nitrofluorobenzene, and the temperature rises to about 28°-30° C. The yellowish suspension is stirred at 30° for 3 hours and at 45° for a further 5 hours until the conversion of the nitrofluorobenzene is complete. Water is then added to the reaction mixture, the pH value is brought to 5 and the chlorobenzene is driven off in vacuo with water, leaving behind a slightly yellow suspension. After cooling down, it is filtered, and the filtercake is washed with water to give N-[2-(4-nitrophenoxy)-ethyl]-benzamide of Example 3: ##STR37##

Workup

  1. customhas formed
  2. customrises to about 28°-30° C
  3. customleaving behind a slightly yellow suspension
  4. temperatureAfter cooling down
  5. filtrationit is filtered
  6. washthe filtercake is washed with water

Sources & evidence

ORD record
ord-6538b7f0dd914467b689eadb4717d6ce
Source dataset
uspto-grants-1989_10
Patent number
US04874857

Reaction notes

Loading…