Ammonium dithiocarbamate → HCID 178459644, compound

HRID 1374443Notes

Reaction equation

HRID 1374443 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH2:10][N:9]([C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12])[CH:8]([CH3:17])[CH2:7][CH:6]=1)=O.[C:18](=[S:21])([S-:20])[NH2:19].[NH4+]>CO.C(N)(=S)C1C=CN=CC=1>[CH3:17][CH:8]1[CH2:7][CH:6]=[C:5]([C:3]2[N:19]=[C:18]([SH:21])[S:20][CH:2]=2)[CH2:10][N:9]1[C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12]

Participants

5

Reactant 2

HCID 11083854Ammonium dithiocarbamateHCID 17857979HCID 17857979, compound

Product 1

HCID 178459644HCID 178459644, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 27237884-PyridinecarbothioamideCatalystHCID 887MethanolSolvent

Procedure

To a solution of allyl 5-(chloroacetyl)-2-methyl-3,6-dihydro-1(2 H)-pyridinecarboxylate (0.50 g, 1.94 mmol) in methanol (10 ml) were added at 0–5° C. thioisonicotinamide (5 mg) and ammonium dithiocarbamate (0.32 g, 2.9 mmol). The reaction mixture was raised to room temperature, stirred for 10 minutes and then stirred at 60–70° C. for 50 minutes. The solvent was removed in vacuo. To the residue was added an aqueous 1N NaOH solution to made alkaline. To the solution were added ethyl acetate and hexane and the solution was separated with a separating funnel. After 6N hydrochloric acid was added to the aqueous layer and ethyl acetate was added thereto, the mixture was again separated with a separating funnel. The aqueous layer was extracted with ethyl acetate. The organic layer was washed twice with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and the solvent was removed in vacuo to give allyl 2-methyl-5-(2-mercapto-1,3-thiazol-4-yl)-3,6-dihydro-1(2 H)-pyridinecarboxylate (368 mg, 64%).

Workup

  1. stirringstirred at 60–70° C. for 50 minutes
  2. customThe solvent was removed in vacuo
  3. additionTo the residue was added an aqueous 1N NaOH solution
  4. additionTo the solution were added ethyl acetate and hexane
  5. customthe solution was separated with a separating funnel
  6. additionAfter 6N hydrochloric acid was added to the aqueous layer and ethyl acetate
  7. additionwas added
  8. customthe mixture was again separated with a separating funnel
  9. extractionThe aqueous layer was extracted with ethyl acetate
  10. washThe organic layer was washed twice with a saturated aqueous sodium chloride solution
  11. dry with materialdried over magnesium sulfate
  12. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-02f5eb6f151c4f3cac1ccdc9784b7d7b
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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