Potassium Hydroxide → 1-(3-Bromophenyl)cyclohexanecarboxamide

HRID 1985108Notes

Reaction equation

HRID 1985108 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-:16].[K+]>C(O)(C)(C)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:14]([NH2:15])=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 43345643HCID 43345643, compound

Product 1

HCID 589094321-(3-Bromophenyl)cyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

With overhead stirrer, a mixture of crude product from step 1, above, (380 g, 1207 mmol), powdered KOH (720 g) and t-BuOH (2.5 L) was heated at reflux overnight. See Hall, J. H.; Gisler, M. A simple method for converting nitriles to amides. Hydrolysis with potassium hydroxide in tert-butyl alcohol. J. Org. Chem. 1976, 41, 3769-3770. If deemed complete by GC analysis, it was cooled with ice-water (cool slowly to avoid shock to the glass), quenched with ice-water (1500 mL). The quenched mixture was then extracted with MTBE (3.5 L+1.5 L). MTBE layers were concentrated to a yellow solid, 390 g.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperaturecool slowly
  4. customquenched with ice-water (1500 mL)
  5. extractionThe quenched mixture was then extracted with MTBE (3.5 L+1.5 L)
  6. concentrationMTBE layers were concentrated to a yellow solid, 390 g

Sources & evidence

ORD record
ord-3cedd4ad77404918b787e475270c4ca1
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

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