Carbon Disulfide → HCID 21453975, compound

HRID 436290Notes

Reaction equation

HRID 436290 reaction equation
[C:1](=[S:3])=[S:2].C(N(CC)CC)C.[O:11]1[CH2:15][CH2:14][NH:13][C:12]21[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2.C([O-])(=O)C.[Zn+2:25].C([O-])(=O)C>CS(C)=O.C(O)(C)C>[O:11]1[CH2:15][CH2:14][NH:13][C:12]21[CH2:20][CH2:19][CH2:18][CH:17]([C:1]([S-:3])=[S:2])[CH2:16]2.[O:11]1[CH2:15][CH2:14][NH:13][C:12]21[CH2:20][CH2:19][CH2:18][CH:17]([C:1]([S-:3])=[S:2])[CH2:16]2.[Zn+2:25]

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 11192Zinc AcetateHCID 2785591-Oxa-4-azaspiro[4.5]decane

Product 1

HCID 21453975HCID 21453975, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3776IsopropanolSolvent

Procedure

Thirty-eight grams (0.50 mole) of carbon disulfide was added with stirring at 10° - 20° C to a mixture of 500 g. isopropanol and 50.5 g. (0.50 mole) triethylamine. To this solution was added 70.5 g. (0.50 mole) of spiro(cyclohexane-1,2'-oxazolidine) [preparation described by A. Cope and E. Hancock, J. Am. Chem. Soc. 64, 1503 (1942)] followed by 46.0 g. (0.25 mole) of anhydrous zinc acetate. The reaction mixture was stirred 4 hours at room temperature. After overnight standing, the precipitate was filtered to give 97.4 g. of the desired carbodithioate melting at 198° - 200° C (decomp.). A sample, dissolved in hot dimethylsulfoxide and precipitated by addition of methanol, melted at 212° - 213° C and had the following analysis: Found: C, 42.80; H, 5.41; N, 5.75; Zn, 12.90%. Calcd for C18H28N2O2S4Zn. C, 43.43; H, 5.63; N, 5.63; Zn, 13.15%.

Workup

  1. additionTo this solution was added 70.5 g
  2. stirringThe reaction mixture was stirred 4 hours at room temperature
  3. filtrationthe precipitate was filtered
  4. customto give 97.4 g
  5. customprecipitated by addition of methanol, melted at 212° - 213° C

Sources & evidence

ORD record
ord-b7a578538b3a48ab9b63805ed47898a9
Source dataset
uspto-grants-1977_02
Patent number
US04008244

Reaction notes

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