Potassium Cyanide → N-(4-amino-4-cyanocyclohexyl)-4-ethoxy-3-methylbenzenesulfonamide

HRID 1944740Notes

Reaction equation

HRID 1944740 reaction equation
[OH-].[NH4+:2].[Cl-].[NH4+:4].[CH2:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH:18]2[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]2)(=[O:16])=[O:15])=[CH:10][C:9]=1[CH3:25])[CH3:6].[C-:26]#N.[K+]>CO.ClCCl.[OH-].[Na+].O>[NH2:2][C:21]1([C:26]#[N:4])[CH2:22][CH2:23][CH:18]([NH:17][S:14]([C:11]2[CH:12]=[CH:13][C:8]([O:7][CH2:5][CH3:6])=[C:9]([CH3:25])[CH:10]=2)(=[O:16])=[O:15])[CH2:19][CH2:20]1

Participants

9

Reactant 4

HCID 9032Potassium CyanideHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 67224104HCID 67224104, compound2×

Product 1

HCID 67224098N-(4-amino-4-cyanocyclohexyl)-4-ethoxy-3-methylbenzenesulfonamide

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A 1:1 mixture of concentrated aqueous ammonium hydroxide (28-30%): water (1606 μl, 6.26 mmol) followed by ammonium chloride (223 mg, 4.17 mmol) was added to 4-ethoxy-3-methyl-N-(4-oxocyclohexyl)benzenesulfonamide (Intermediate 122, 650 mg, 2.087 mmol) in methanol. The reaction was stirred for a few minutes then potassium cyanide (272 mg, 4.17 mmol) was added in one portion. After 18 hours the reaction was diluted with dichloromethane and 5N sodium hydroxide followed by water was added to make the aqueous layer pH 12. The aqueous layer was extracted fives times with dichloromethane. TLC (50% ethyl acetate in heptane) suggested a small amount starting material was present, but a major UV spot was just off baseline. Combined organic layers were dried over sodium sulfate, filtered, and concentrated, to yield crude N-(4-amino-4-cyanocyclohexyl)-4-ethoxy-3-methylbenzenesulfonamide (770 mg, 2.282 mmol) which was used without further purification. LCMS [M+H]=338.3.

Workup

  1. additionwas added
  2. extractionThe aqueous layer was extracted fives times with dichloromethane
  3. dry with materialCombined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-24a527eab6e54ea68887338fb683efbb
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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