Cyclohexylamine → N-cyclohexyl-4-(4-nitrophenoxy)benzenesulfonamide

HRID 1156941Notes

Reaction equation

HRID 1156941 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:21]1([NH2:27])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:27][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 11430Potassium CarbonateHCID 12249742HCID 12249742, compound

Product 1

HCID 1067811N-cyclohexyl-4-(4-nitrophenoxy)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-(4-Nitrophenoxy)benzenesulphonyl chloride (Example 1) (18.8 g), cyclohexylamine (6.5 g), anhydrous potassium carbonate (8.3 g) and acetone (100 ml) were refluxed together for 4 hours. On concentration and addition of water, an oil separated which solidified overnight. From ethanol on addition of light petroleum (b.p. 60°-80° C.), 4-(4-nitrophenoxy)-N-cyclohexylbenzenesulphonamide was obtained in the form of crystals, m.p. 94° C.

Workup

  1. concentrationOn concentration and addition of water
  2. customan oil separated which
  3. additionFrom ethanol on addition of light petroleum (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-40368decc896441ba6ffe84333a7cd44
Source dataset
uspto-grants-1982_06
Patent number
US04337274

Reaction notes

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