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Sodium Hydroxide → 2'-Bromo-4'-nitro-1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexanecarboxanilide, tetra-n-propylammonium salt

HRID 981834
Notes
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Reaction equation

HRID 981834 reaction equation
[Br:1][C:2]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:3]=1[NH:4][C:5]([C:7]1([F:23])[C:12]([F:14])([F:13])[C:11]([F:16])([F:15])[C:10]([F:18])([F:17])[C:9]([F:20])([F:19])[C:8]1([F:22])[F:21])=[O:6].[OH-].[Na+]>[Br-].C([N+](CCC)(CCC)CCC)CC.CC(C)=O>[CH2:3]([N+:4]([CH2:3][CH2:24][CH3:25])([CH2:5][CH2:7][CH3:12])[CH2:5][CH2:7][CH3:8])[CH2:2][CH3:27].[Br:1][C:2]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:3]=1[NH:4][C:5]([C:7]1([F:23])[C:12]([F:13])([F:14])[C:11]([F:15])([F:16])[C:10]([F:17])([F:18])[C:9]([F:19])([F:20])[C:8]1([F:21])[F:22])=[O:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 163772Cyclohexanecarboxamide, N-(2-bromo-4-nitrophenyl)-1,2,2,3,3,4,4,5,5,6,6-undecafluoro-

Product 1

HCID 1317167992'-Bromo-4'-nitro-1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexanecarboxanilide, tetra-n-propylammonium saltYield 75.9%

Reagents, catalysts & solvents 2

HCID 74745Tetrapropylammonium bromideCatalyst
HCID 180
Acetone
Solvent

Procedure

2'-Bromo-4'-nitro-1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexanecarboxanilide (2.6 grams; 0.005 mole) was dissolved in 50 ml. of acetone and 1N sodium hydroxide (5.0 ml., 0.005 mole) was added all at once. Tetrapropylammonium bromide (1.35 gram; 0.005 mole) was then added and the reaction mixture was stirred until it became one phase. The reaction mixture was then poured over ice/water, and an oily solid separated. It was extracted with diethyl ether, dried over magnesium sulfate, evaporated, and crystallized at -10° C. from water/ethanol. 0.9 gram (25% yield) of the tetra-n-propylammonium salt was obtained, m.p., 86°-87° C.

Workup

  1. customan oily solid separated
  2. extractionIt was extracted with diethyl ether
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customcrystallized at -10° C. from water/ethanol

Sources & evidence

ORD record
ord-e28ce42df09c478ebdb755a6013bbde6
Source dataset
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04992471

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes