Cyclohexanone → HCID 66618606, compound

HRID 1966957Notes

Reaction equation

HRID 1966957 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]1(=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C[Si]([C:20]#[N:21])(C)C>C(O)(=O)C>[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:9]2([C:20]#[N:21])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 108934-IodoanilineHCID 82115Trimethylsilyl cyanide

Product 1

HCID 66618606HCID 66618606, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3 g (13.7 mmol, 1 eq.) of 4-iodoaniline are added to a solution of 1.4 ml (13.5 mmol, 1 eq.) of cyclohexanone in 20 ml of acetic acid at 0° C. The solution is stirred for a moment, and 1.8 ml (13.5 mmol, 1 eq.) of trimethylsilyl cyanide are added. The reaction medium is stirred overnight at room temperature. It is then poured gently into ice-cold ammonium hydroxide solution and extracted with dichloromethane. The organic phases are combined and washed with water. They are dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel. The product 1-(4-iodophenylamino)cyclohexanecarbonitrile is obtained in the form of a white solid.

Workup

  1. additionare added
  2. additionIt is then poured gently into ice-cold ammonium hydroxide solution
  3. extractionextracted with dichloromethane
  4. washwashed with water
  5. dry with materialThey are dried over sodium sulfate
  6. customThe solvents are evaporated off
  7. customthe residue is then chromatographed on silica gel

Sources & evidence

ORD record
ord-427f19b7c1c44811b2d58715bc81be3b
Source dataset
uspto-grants-2013_04
Patent number
US08420682B2

Reaction notes

Loading…