Carbon Disulfide → HCID 21454007, compound

HRID 436289Notes

Reaction equation

HRID 436289 reaction equation
Cl.[CH3:2][C:3]1([CH3:8])[NH:7][CH2:6][CH2:5][S:4]1.C(N(CC)CC)C.[C:16](=[S:18])=[S:17].C([O-])(=O)C.[Zn+2:23].C([O-])(=O)C>C(O)(C)C>[CH3:2][C:3]1([CH3:8])[N:7]([C:16]([S-:18])=[S:17])[CH2:6][CH2:5][S:4]1.[CH3:2][C:3]1([CH3:8])[N:7]([C:16]([S-:18])=[S:17])[CH2:6][CH2:5][S:4]1.[Zn+2:23]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 11192Zinc AcetateHCID 1203862,2-Dimethyl-1,3-thiazolidine--hydrogen chloride (1/1)

Product 1

HCID 21454007HCID 21454007, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
10 °C

Procedure

While cooling and stirring at 10° C, 76.8 g. (0.50 mole) 2,2-dimethylthiazolidine hydrochloride [preparation described by B. Sweetman et al. J. Med. Chem. 12, 888 (1969)] was added to a mixture of 30 ml isopropanol and 101 g. (1.00 mole) triethylamine. Likewise, 38.0 g. (0.50 mole) of carbon disulfide was gradually added, followed by 45.8 g. (0.25 mole) of anhydrous zinc acetate. After standing ovenight at room temperature, the precipitate was filtered, twice water-washed with 1 liter portions of water and air-dried to give 80.5 g. of the yellow product melting at 148° - 153° C (decomp.) and having the following analysis: Found: C, 31.51; H, 4.70%. Calcd for C12H20N2S6Zn: C, 32.04; H, 4.45%.

Workup

  1. temperatureWhile cooling
  2. customAfter standing ovenight at room temperature
  3. filtrationthe precipitate was filtered
  4. washtwice water-washed with 1 liter portions of water
  5. customair-dried
  6. customto give 80.5 g

Sources & evidence

ORD record
ord-46cd78d527ee4463aa74dbb2369a644b
Source dataset
uspto-grants-1977_02
Patent number
US04008244

Reaction notes

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