Ammonium dithiocarbamate → HCID 178459659, compound

HRID 1374422Notes

Reaction equation

HRID 1374422 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH2:6][C@@H:7]([CH3:17])[N:8]([C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12])[CH2:9][CH:10]=1)=O.[C:18](=[S:21])([S-:20])[NH2:19].[NH4+]>CO.C(N)(=S)C1C=CN=CC=1>[SH:21][C:18]1[S:20][CH:2]=[C:3]([C:5]2[CH2:6][C@@H:7]([CH3:17])[N:8]([C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12])[CH2:9][CH:10]=2)[N:19]=1

Participants

5

Reactant 2

HCID 11083854Ammonium dithiocarbamateHCID 11821250HCID 11821250, compound

Product 1

HCID 178459659HCID 178459659, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 27237884-PyridinecarbothioamideCatalystHCID 887MethanolSolvent

Procedure

To a solution of allyl (2R)-4-(chloroacetyl)-2-methyl-3,6-dihydro-1(2 H)-pyridinecarboxylate (0.255 g, 1.0 mmol) in methanol (5 ml) were added at 0–5° C. thioisonicotinamide (5 mg) and ammonium dithiocarbamate (0.22 g, 2.0 mmol). The reaction mixture was raised to room temperature, stirred for 15 minutes and then stirred at 55–60° C. for 1.5 hour. The solvent was removed in vacuo and to the residue was added aqueous 1N NaOH solution to make the solution alkaline. To the solution were added ethyl acetate and hexane, and the mixture was separated with a separating funnel. The aqueous layer was acidified with 6N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed twice with a saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed in vacuo to give allyl (2R)-4-(2-mercapto-1,3-thiazol-4-yl)-2-methyl-3,6-dihydro-1(2 H)-pyridinecarboxylate (170 mg, 59%).

Workup

  1. stirringstirred at 55–60° C. for 1.5 hour
  2. customThe solvent was removed in vacuo and to the residue
  3. additionwas added aqueous 1N NaOH solution
  4. additionTo the solution were added ethyl acetate and hexane
  5. customthe mixture was separated with a separating funnel
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed twice with a saturated aqueous sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-087336b2f59d4c779f7832152d1c00ac
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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