Carbon Disulfide → HCID 21453991, compound

HRID 1287971Notes

Reaction equation

HRID 1287971 reaction equation
Cl.[S:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.[C:7](=[S:9])=[S:8].C([O-])(=O)C.[Zn+2:14].C([O-])(=O)C>N1C=CC=CC=1>[S:2]1[CH2:6][CH2:5][N:4]([C:7]([S-:9])=[S:8])[CH2:3]1.[S:2]1[CH2:6][CH2:5][N:4]([C:7]([S-:9])=[S:8])[CH2:3]1.[Zn+2:14]

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 11192Zinc AcetateHCID 12444283HCID 12444283, compound

Product 1

HCID 21453991HCID 21453991, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

While cooling and stirring 250 g. of pyridine, 175 g. (1.40 moles) of thiazolidine hydrochloride [preparation described by S. Ratner and H. Clarke, J. Am. Chem. Soc. 59, 200 (1937)] was added. After it had dissolved, 106.4 g. (1.40 mole) of carbon disulfide was added dropwise, followed by 128.5 g. (0.70 mole) of anhydrous zinc acetate. The resulting reaction mixture was stirred at 40° - 50° C for 2 hours. The precipitate was filtered at 5° - 10° C. The crude solid was water-washed and finally freed of pyridine by vacuum-drying at 120° C to give 147.8 g. of the desired product. It gradually decomposed starting at ca. 200° C without a definite final decomposition point. A small sample washed with hot benzene had the following analysis:

Workup

  1. temperatureWhile cooling
  2. dissolutionAfter it had dissolved
  3. customThe resulting reaction mixture
  4. stirringwas stirred at 40° - 50° C for 2 hours
  5. filtrationThe precipitate was filtered at 5° - 10° C
  6. washwashed
  7. customby vacuum-drying at 120° C
  8. customto give 147.8 g

Sources & evidence

ORD record
ord-e4281f4961cb4046bd8ff0ad04da1aea
Source dataset
uspto-grants-1976_10
Patent number
US03987017

Reaction notes

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