Hydrochloric Acid → HCID 59356299, compound

HRID 1046955Notes

Reaction equation

HRID 1046955 reaction equation
[SH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[C:13](=[S:15])=[S:14].Cl[CH2:17][C:18]#[N:19].Cl>C(#N)C.C(OCC)(=O)C.CCCCCC.O>[C:13](=[S:15])([S:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])[S:14][CH2:17][C:18]#[N:19]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 65143-Mercaptopropionic AcidHCID 7856ChloroacetonitrileHCID 11430Potassium Carbonate

Product 1

HCID 59356299HCID 59356299, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

3-Mercaptopropionic acid (5.3 g, 0.05 mol) was added within 10 minutes to a stirring suspension of potassium carbonate (7.0 g, 0.051 mol) in acetonitrile (40 mL) at room temperature. The reaction mixture was added carbon disulfide (3.8 g, 0.05 mol). The resulting yellow mixture was kept stirring for two hours and then added chloroacetonitrile (3.78 g, 0.05 mol). The resulting mixture was allowed to stir at room temperature for further one hour. Water (50 mL) was added, the yellow aqueous solution was acidified with dilute hydrochloric acid until pH˜2 and extracted with diethyl ether (50 mL×2). The organic layer was dried over anhydrous magnesium sulfate. After removal of solvent, the product cyanomethyl carboxyethyl trithiocarbonate was obtained as a yellow solid (6.4 g, 58% yield) after column chromatography (silica-gel; ethyl acetate: n-hexane 3:7 as solvent). 1H NMR (CDCl3) δ 2.85 (t, 2H, HOOCCH2); 3.65 (t, 2H, CH2S); 4.15 (s, 2H, NCCH2S), 8.20 (br s, 1H, COOH). 13C NMR (CDCl3) δ 21.5, 31.7, 32.5, 114.6, 176.9, 218.3.

Workup

  1. stirringto stir at room temperature for further one hour
  2. extractionextracted with diethyl ether (50 mL×2)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customAfter removal of solvent

Sources & evidence

ORD record
ord-dcbc8922cdd84cb2b1b0bffeb39a6bdf
Source dataset
uspto-grants-2013_10
Patent number
US08569441B2

Reaction notes

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