Diisopropylethylamine → 1-phenyl-N-(2-nitrophenyl)cyclohexanecarboxamide

HRID 1420577

Reaction equation

HRID 1420577 reaction equation
[CH3:1][C:2]1([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-:19])=[O:18])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[C:20]1(C2(C(Cl)=O)CCCCC2)[CH:25]=[CH:24]C=[CH:22][CH:21]=1.CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[C:1]1([C:2]2([C:8]([NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N+:17]([O-:19])=[O:18])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[CH:24]=[CH:25][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 103535371-Phenylcyclohexanecarbonyl chlorideHCID 22458203HCID 22458203, compound

Product 1

HCID 187823111-phenyl-N-(2-nitrophenyl)cyclohexanecarboxamideYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

This compound was prepared following the procedure described for compound 39A in example 39, except that 1-phenylcyclohexanecarbonyl chloride (J. Am. Chem. Soc. 68, 2345-7 (1946)) was used in place of 1-methylcyclohexanecarbonyl chloride, toluene in place of CH2Cl2, DIPEA in place of triethylamine and reaction mixture was refluxed for 15 h. The crude was purified by flash chromatography (petroleum ether-EtOAc 98:2). Yield 91%.

Workup

  1. customThis compound was prepared
  2. temperaturewas refluxed for 15 h
  3. customThe crude was purified by flash chromatography (petroleum ether-EtOAc 98:2)

Sources & evidence

ORD record
ord-4b2e0c04a17c4d4389f9e9c5ea5374a0
Source dataset
uspto-grants-2000_06
Patent number
US06071920

Linked notes

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