Carbon Disulfide → HCID 21454004, compound

HRID 436291Notes

Reaction equation

HRID 436291 reaction equation
C(N(CC)CC)C.[C:8](=[S:10])=[S:9].C([O-])(=O)C.[Zn+2:15].C([O-])(=O)C.[CH3:20][CH:21]1[O:25][CH:24]([C:26]([Cl:29])([Cl:28])[Cl:27])[NH:23][CH2:22]1.[Zn]>O>[CH3:20][CH:21]1[O:25][CH:24]([C:26]([Cl:29])([Cl:28])[Cl:27])[N:23]([C:8]([S-:10])=[S:9])[CH2:22]1.[CH3:20][CH:21]1[O:25][CH:24]([C:26]([Cl:29])([Cl:28])[Cl:27])[N:23]([C:8]([S-:10])=[S:9])[CH2:22]1.[Zn+2:15]

Participants

7

Reactant 5

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 11192Zinc AcetateHCID 23994Zinc2×HCID 203446715-Methyl-2-(trichloromethyl)-1,3-oxazolidine

Product 1

HCID 21454004HCID 21454004, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 412.0 g. (4.0 moles) triethylamine, 60.8 g. (0.8 mole) carbon disulfide, 73.2 g. (0.4 mole) anhydrous zinc acetate and 163.6 g. (0.8 mole) 5-methyl-2-trichloromethyloxazolidine was stirred at 40° C. for 1 hour. After standing overnight at room temperature, the reaction mixture was diluted with water and filtered to give 417.8 g. of the desired crude product sintering at 89° C. and melting with decomposition at 128°-150° C. Extraction with chloroform and repeated crystallization from benzene gave an analytical sample melting at 170°-176° C. with decomposition. It had the following analysis: Found: N, 4.30; Zn, 10.16. Calc. for C12H14Cl6N2O2S4Zn: N, 4.48; Zn, 10.47.

Workup

  1. additionA mixture of 412.0 g
  2. filtrationfiltered
  3. customto give 417.8 g
  4. customat 89° C.
  5. custommelting with decomposition at 128°-150° C
  6. extractionExtraction with chloroform
  7. customcrystallization from benzene
  8. customgave an analytical sample melting at 170°-176° C. with decomposition

Sources & evidence

ORD record
ord-15849cc5895d4d4492a93bbd435556a6
Source dataset
uspto-grants-1977_02
Patent number
US04008244

Reaction notes

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