Carbon Disulfide → HCID 178527790, compound

HRID 2399719Notes

Reaction equation

HRID 2399719 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[S]Cl.[C:11](=[S:13])=[S:12]>C(O)(=O)C.CCCCCC>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]2[N:6]=[C:11]([SH:13])[S:12][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 78124-ChloroanilineHCID 15930840CID 15930840

Product 1

HCID 178527790HCID 178527790, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8058HexaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 4-chloroaniline (2.55 g) in acetic acid (5 cm3) was added sulphur monochloride (10 cm3) causing formation of a thick red slurry. The reaction was heated at 60° C. for 4 hours giving a mixture of green solid and a green solution. The mixture was diluted with hexane and the green solid was filtered off. The solid was taken into water and 2M NaOH was added and the mixture heated for 4 hours at 100° C. and then filtered through celite to give a pale pink filtrate. Carbon disulphide (2 cm3) was added to the filtrate and the reaction was heated at reflux for 15 hours. The mixture was cooled and acidlied to pH 1 causing formation of a thick yellow precipitate. Filtration and recrystallisation from ethanol/acetone/water gave 6-chloro-2-mercaptobenzthiazole as a white solid. 1H NMR (DMSO): d 7.97 (1H, d), 7.58 (1H, dd), 7.41 (1 H, d). Mp 251°-253° C. (dec).

Workup

  1. customgiving
  2. additiona mixture of green solid
  3. filtrationthe green solid was filtered off
  4. additionwas added
  5. temperaturethe mixture heated for 4 hours at 100° C.
  6. filtrationfiltered through celite
  7. customto give a pale pink filtrate
  8. temperaturethe reaction was heated
  9. temperatureat reflux for 15 hours
  10. temperatureThe mixture was cooled
  11. filtrationFiltration and recrystallisation from ethanol/acetone/water

Sources & evidence

ORD record
ord-7af06c3180f842efb2af6d9c06484db4
Source dataset
uspto-grants-1995_09
Patent number
US05451594

Reaction notes

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