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

HRID 1007680

Reaction equation

HRID 1007680 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 dropwise 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 dropwise
  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-cd8ed3b76729498d81ad267c848cbbe7
Source dataset
uspto-grants-2004_09
Patent number
US06794404B2

Linked notes

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