Carbon Disulfide → HCID 178424119, compound

HRID 267996Notes

Reaction equation

HRID 267996 reaction equation
[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1.[S].[C:10](=[S:12])=[S:11]>>[SH:12][C:10]1[S:11][C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([CH3:8])[C:2]=2[N:1]=1

Participants

4

Reactant 3

HCID 6348Carbon DisulfideHCID 7242O-ToluidineHCID 5362487Sulfur

Product 1

HCID 178424119HCID 178424119, compoundYield 46%

Procedure

Into a 500 ml reactor were charged o-toluidine (27 g), sulfur (8g), and carbon disulfide (22 g). Seventy minutes of electrically heating the system was required to elevate the temperature to 275°C (240 psig original pressure at 275°C). After 21/2 hours at 275°C (the pressure leveled out at 470 psig in 90 minutes) the heat source was removed and the reactor was cooled. The reaction mixture was mixed with 200 g water containing 16 g sodium hydroxide. Tar-like residue (18.5 g) was removed by decantation. Acidification of decantate with hydrochloric acid and filtration of the resulting mixture gave 21 g (46 percent yield) of crude 2-mercapto-4-methylbenzothiazole (m.p. 161°-173°C).

Workup

  1. temperatureSeventy minutes of electrically heating the system
  2. customto 275°C
  3. custom(240 psig original pressure at 275°C)
  4. custom) the heat source was removed
  5. temperaturethe reactor was cooled
  6. additionThe reaction mixture was mixed with 200 g water containing 16 g sodium hydroxide
  7. customTar-like residue (18.5 g) was removed by decantation
  8. filtrationAcidification of decantate with hydrochloric acid and filtration of the resulting mixture

Sources & evidence

ORD record
ord-23ba710bd7f3433e8734e168d447ff38
Source dataset
uspto-grants-1976_03
Patent number
US03946030

Reaction notes

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