Water → HCID 23371869, compound

HRID 1900086Notes

Reaction equation

HRID 1900086 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C1(C)C=CC(S([CH2:24][N+:25]#[C-])(=O)=O)=CC=1.O.[Cl-].[Na+]>COCCOC.C(O)C>[C:24]([CH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1)#[N:25]

Participants

7

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 161915Tosylmethyl isocyanideHCID 233718944-(4-Aminophenyl)cyclohexan-1-one

Product 1

HCID 23371869HCID 23371869, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

392 mg (3.5 mmol) of potassium t-butylate were added portionwise at -10° to a suspension of 278 mg (1.5 mmol) of 4-(4-oxo-cyclohexyl)-aniline and 370 mg (1.9 mmol) of toluene-4-sulfonylmethylisocyanide in 5 ml of 1,2-dimethoxyethane and 0.15 ml of ethanol. After stirring at -5° for 1 hour and at room temperature for a further 70 hours 25 ml of water and 10 ml of saturated sodium chloride solution were added and the mixture was extracted three times with 40 ml of dichloromethane each time. The organic phase was dried with sodium sulfate and concentrated. Chormatography over silica gel with ethyl acetate/hexane 1:2 gave 165 mg (56%) of 4-(4-cyano-cyclohexyl)-aniline with m.p. 132°-140°.

Workup

  1. additionwere added
  2. extractionthe mixture was extracted three times with 40 ml of dichloromethane each time
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-eac76925a80c4474b63b144e45559c3a
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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