Carbon Disulfide → HCID 21453983, compound

HRID 436294Notes

Reaction equation

HRID 436294 reaction equation
C(N(CC)CC)C.C([O-])(=O)C.[Zn+2:12].C([O-])(=O)C.[C:17]1([CH:23]2[O:27][CH:26]([C:28]([Cl:31])([Cl:30])[Cl:29])[NH:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:32](=[S:34])=[S:33]>>[C:17]1([CH:23]2[O:27][CH:26]([C:28]([Cl:31])([Cl:30])[Cl:29])[N:25]([C:32]([S-:34])=[S:33])[CH2:24]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1.[C:17]1([CH:23]2[O:27][CH:26]([C:28]([Cl:31])([Cl:30])[Cl:29])[N:25]([C:32]([S-:34])=[S:33])[CH2:24]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1.[Zn+2:12]

Participants

5

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 11192Zinc AcetateHCID 234551115-Phenyl-2-(trichloromethyl)-1,3-oxazolidine

Product 1

HCID 21453983HCID 21453983, compoundYield 58%

Conditions

Temperature
50 °C

Procedure

A mixture of 30.3 g (0.3 mole) triethylamine, 18.3 g. (0.1 mole) zinc acetate, 55.0 g. (0.206 mole) 5-phenyl-2-trichloromethyloxazolidine and 15.6 g. (0.206 mole) carbon disulfide was stirred at ambient temperatures for 17 hours and then was heated at 50° C, for 3 hours. A reddish amber-colored semi-solid was obtained after the volatile materials were distilled off at 50°/25 mm. Hg. The semi-solid was dissolved in methanol and the resulting solution added to water with vigorous stirring. The solids were filtered, air-dried, and redissolved in benzene. After drying the solution with magnesium sulfate, filtering the mixture and evaporating the solvent, 37 g. (58%) of the desired product (m.p. 91°-93° C.) was obtained; its infrared spectrum was consistent with the structure: Found: N, 3.86. Calc. for C22H18Cl6N2O2S4Zn: N, 3.74.

Workup

  1. customA reddish amber-colored semi-solid was obtained after the volatile materials
  2. distillationwere distilled off at 50°/25 mm. Hg
  3. dissolutionThe semi-solid was dissolved in methanol
  4. additionthe resulting solution added to water with vigorous stirring
  5. filtrationThe solids were filtered
  6. customair-dried
  7. dissolutionredissolved in benzene
  8. dry with materialAfter drying the solution with magnesium sulfate
  9. filtrationfiltering the mixture
  10. customevaporating the solvent, 37 g

Sources & evidence

ORD record
ord-3c75c3d110ed4fa8a0bd993a9ea9c800
Source dataset
uspto-grants-1977_02
Patent number
US04008244

Reaction notes

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