Potassium thiocyanate → HCID 178501269, compound

HRID 1035728Notes

Reaction equation

HRID 1035728 reaction equation
[S-]C#N.[K+].[CH:5]1([O:10][CH2:11][C:12]([NH:14][NH2:15])=O)[CH2:9][CH2:8][CH2:7][CH2:6]1.[N:16]([C:19]([C:21]1[CH:37]=[CH:36][C:24]([O:25][C@@H:26]2[CH2:31][CH2:30][C@H:29]([C:32]([O:34][CH3:35])=[O:33])[CH2:28][CH2:27]2)=[CH:23][CH:22]=1)=[O:20])=[C:17]=[S:18]>C(#N)C>[CH:5]1([O:10][CH2:11][C:12]2[S:18][C:17]([NH:16][C:19]([C:21]3[CH:37]=[CH:36][C:24]([O:25][C@@H:26]4[CH2:27][CH2:28][C@H:29]([C:32]([O:34][CH3:35])=[O:33])[CH2:30][CH2:31]4)=[CH:23][CH:22]=3)=[O:20])=[N:15][N:14]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 516872Potassium thiocyanateHCID 607822732-(Cyclopentyloxy) acetohydrazideHCID 178501271HCID 178501271, compound

Product 1

HCID 178501269HCID 178501269, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

0.4 g of cis-4-(4-methoxycarbonylcyclohexyloxy)benzoic acid is placed in 10 mL of dichloromethane with stirring, at room temperature, under a nitrogen atmosphere. 0.18 mL of oxalyl chloride (2.16 mmol, 1.5 eq.) and 2 drops of dimethylformamide are successively added. The reaction medium is stirred for 2 hours and concentrated under vacuum. The methyl cis-4-(4-chlorocarbonylphenoxy)cyclohexanecarboxylate formed is dissolved in 15 mL of acetonitrile and placed under nitrogen. The mixture is cooled in an ice bath and 0.210 g of potassium thiocyanate (2.16 mmol, 1.5 eq.) is added. The reaction mixture is stirred at room temperature for 1 hour 30 minutes. 0.455 g of cyclopentyloxyacetic acid hydrazide (2.87 mmol, 2 eq.) dissolved in 5 mL of acetonitrile is then added to the methyl cis-4-(4-isothiocyanatocarbonylphenoxy)cyclohexanecarboxylate obtained and the mixture is refluxed for 2 hours 30 minutes and then left to stand at room temperature for 36 hours. The precipitate formed is filtered off and washed with acetonitrile. 0.450 g of methyl cis-4-[4-(5-cyclopentyloxymethyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenoxy]cyclohexanecarboxylate is obtained.

Workup

  1. temperatureThe mixture is cooled in an ice bath
  2. customobtained
  3. temperaturethe mixture is refluxed for 2 hours 30 minutes
  4. waitleft
  5. waitto stand at room temperature for 36 hours
  6. customThe precipitate formed
  7. filtrationis filtered off
  8. washwashed with acetonitrile

Sources & evidence

ORD record
ord-45eb3d171fd248978adea2db9314bf9f
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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