Potassium Hydroxide → 4-(Cyclohexylmethyl)thio-2-nitroaniline

HRID 616919Notes

Reaction equation

HRID 616919 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([S:11][C:12]#N)[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[BH4-].[Na+].[OH-].[K+].[CH:18]1(CBr)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(O)C.C(Cl)(Cl)Cl.O>[CH:18]1([CH2:12][S:11][C:9]2[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

8

Reactant 4

HCID 14797Potassium HydroxideHCID 1046774-Amino-3-nitrophenyl thiocyanateHCID 137636Cyclohexane, (bromomethyl)-HCID 4311764Sodium borohydride

Product 1

HCID 205328424-(Cyclohexylmethyl)thio-2-nitroaniline

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent3×HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 9.75 g (0.05 mole) of 2-nitro-4-thiocyanoaniline in 500 ml of absolute ethanol under nitrogen there is added 2.04 g (0.05 mole) of sodium borohydride in portions. The mixture is stirred at room temperature for 15 minutes and then refluxed for 15 minutes. The heating mantle is removed and 3.25 g (0.05 mole) of KOH in 15 ml of absolute ethanol is added. The mixture is stirred for 1 minute. A solution of 8.85 g (0.05 mole) of cyclohexylmethyl bromide in 15 ml of absolute ethanol is added and the mixture is stirred at room temperature for 15 minutes then refluxed for 1 hour. Equal amounts of water and CHCl3 are added until 2 layers are formed. The organic layer is separated, dried (MgSO4) and the solvent removed in vacuo. The residue is crystallized from ethyl ether to yield 8.3 g, m.p. 80°-82°.

Workup

  1. temperaturerefluxed for 15 minutes
  2. customThe heating mantle is removed
  3. stirringThe mixture is stirred for 1 minute
  4. stirringthe mixture is stirred at room temperature for 15 minutes
  5. temperaturethen refluxed for 1 hour
  6. customare formed
  7. customThe organic layer is separated
  8. dry with materialdried (MgSO4)
  9. customthe solvent removed in vacuo
  10. customThe residue is crystallized from ethyl ether
  11. customto yield 8.3 g, m.p. 80°-82°

Sources & evidence

ORD record
ord-8366cb85e2c34ea5b7e21c284e17fad8
Source dataset
uspto-grants-1978_02
Patent number
US04076828

Reaction notes

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