18-Crown-6 → HCID 87552636, compound

HRID 1970197Notes

Reaction equation

HRID 1970197 reaction equation
CC(C)([O-])C.[K+].C1OCCOCCOCCOCCOCCOC1.[CH2:25]([N:27]([CH3:39])[CH:28]=[N:29][C:30]1[CH:35]=[C:34]([CH3:36])[C:33]([OH:37])=[CH:32][C:31]=1[CH3:38])[CH3:26].[CH3:40][O:41][N:42]=[C:43]1[CH2:48][CH2:47][CH2:46][CH2:45][CH:44]1Cl>CS(C)=O.O>[CH2:25]([N:27]([CH3:39])[CH:28]=[N:29][C:30]1[CH:35]=[C:34]([CH3:36])[C:33]([O:37][CH:44]2[CH2:45][CH2:46][CH2:47][CH2:48][C:43]2=[N:42][O:41][CH3:40])=[CH:32][C:31]=1[CH3:38])[CH3:26]

Participants

7

Reactant 4

HCID 2855718-Crown-6HCID 23665647Potassium tert-butoxideHCID 60135688HCID 60135688, compoundHCID 73799249HCID 73799249, compound

Product 1

HCID 87552636HCID 87552636, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

At from 0 to 5° C., 239 mg (2.13 mmol) of potassium tert-butoxide and 26 mg 18-crown-6 (0.10 mmol) were added a little at a time and with stirring to 200 mg (0.97 mmol) of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylformamidine (cf. WO 2007/031513) in 3 ml of DMSO, and stirring was continued for about 15 minutes. At from 0 to 5° C., a solution of 313 mg (1.94 mmol) of 2-chlorocyclohexanone O-methyl oxime in 0.5 ml of DMSO was added to this mixture with stirring, and stirring was continued for about 20 hours at from 20 to 25° C. With cooling and a little at a time, 50 ml of water were added, and the mixture was extracted with MTBE. The combined organic phases were dried and then freed from the solvent. Cheomatography on alumina using cyclohexane/MTBE mixtures gave 100 mg of the title compound.

Workup

  1. stirringwith stirring
  2. stirringstirring
  3. waitwas continued for about 20 hours at from 20 to 25° C
  4. temperatureWith cooling
  5. extractionthe mixture was extracted with MTBE
  6. customThe combined organic phases were dried

Sources & evidence

ORD record
ord-575a895fde3c4be7a36e24325636ff9b
Source dataset
uspto-grants-2013_04
Patent number
US08426631B2

Reaction notes

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