tert-butyl N-(4-oxocyclohexyl)carbamate → HCID 9837225, compound

HRID 545563Notes

Reaction equation

HRID 545563 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)(C)(C)C.Cl.[C:17]([C:19]1[CH:24]=[CH:23][C:22]([NH:25]N)=[CH:21][CH:20]=1)#[N:18]>Cl.O>[NH2:7][CH:8]1[CH2:13][CH2:12][C:11]2[NH:25][C:22]3[CH:23]=[CH:24][C:19]([C:17]#[N:18])=[CH:20][C:21]=3[C:10]=2[CH2:9]1

Participants

5

Reactant 2

HCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 162129624-Cyanophenylhydrazine Hydrochloride

Product 1

HCID 9837225HCID 9837225, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

Combine (4-oxocyclohexyl)carbamic acid tert-butyl ester (40.9 g, 192 mmol) and 4-cyanophenylhydrazine hydrochloride (25.0 g, 147 mmol) in concentrated hydrochloric acid (100 mL) and water (200 mL) and heat at reflux for 18 h. Allow to cool and collect the precipitate. Wash with Na2CO3 solution and azetrope with CHCl3, absolute EtOH, and CHCl3 again to obtain 25.5 g of a white solid (82%). MS (ES): m/z 212 (M+1).

Workup

  1. temperatureat reflux for 18 h
  2. temperatureto cool
  3. customcollect the precipitate
  4. washWash with Na2CO3 solution and azetrope with CHCl3, absolute EtOH, and CHCl3 again

Sources & evidence

ORD record
ord-5901b4c56a304b54ab0c382245c57cf5
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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