Water → Ethyl 4-(cyclohexylamino)-3-nitrobenzoate

HRID 1018239

Reaction equation

HRID 1018239 reaction equation
Cl[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH:16]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.O>CS(C)=O>[CH2:9]([O:8][C:6](=[O:7])[C:5]1[CH:11]=[CH:12][C:2]([NH:22][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:3]([N+:13]([O-:15])=[O:14])[CH:4]=1)[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 7965CyclohexylamineHCID 1268247Ethyl 4-chloro-3-nitrobenzoate

Product 1

HCID 5298559Ethyl 4-(cyclohexylamino)-3-nitrobenzoateYield 100.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 4-chloro-3-nitrobenzoate (20.00 g, 87 mmol) was dissolved in DMSO (50 mL) and cyclohexylamine (2.1 equiv. 21 mL, 183 mmol) was added and the mixture stirred at 60° C. for 5 h. After cooling to ambient temperature, the reaction mixture was added drop-wise with vigorous stirring to water (500 mL). After stirring for an additional 15 min, the precipitated solid was collected by filtration, washed with water and dried. The title compound (25.67 g, 100% yield) was obtained as a bright yellow solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. additionthe reaction mixture was added drop-wise
  3. stirringAfter stirring for an additional 15 min
  4. filtrationthe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-2b11167d32d541469216a7d27cf8de35
Source dataset
uspto-grants-2002_11
Patent number
US06479508B1

Linked notes

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