Chloroacetonitrile → 2-(2-Benzothiazolylthio)acetonitrile

HRID 435725Notes

Reaction equation

HRID 435725 reaction equation
[SH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.CC(C)([O-])C.[K+].Cl[CH2:18][C:19]#[N:20]>O1CCCC1>[C:19]([CH2:18][S:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1)#[N:20]

Participants

5

Procedure

In a 1 liter flask were combined 33.4 g. (0.2 mole) of 2-mercaptobenzothiazole and 22.4 g. (0.2 mole) of potassium t-butoxide with 300 ml. of tetrahydrofuran. The reaction mass was stirred at room temperature for 15 minutes. Chloroacetonitrile, 16 g. (0.2 mole) was added and the resulting mixture was stirred at room temperature for 1 hour. The mixture was then poured into 400 ml. of benzene and was washed with three 250 ml. portions of water. The benzene phase was dried with anhydrous magnesium sulfate. The solvent was evaporated. There was obtained a yield of 37.2 g. of the title compound, m.p. 75°-77° C.

Workup

  1. customIn a 1 liter flask were combined
  2. addition(0.2 mole) was added
  3. stirringthe resulting mixture was stirred at room temperature for 1 hour
  4. additionThe mixture was then poured into 400 ml
  5. washof benzene and was washed with three 250 ml
  6. dry with materialThe benzene phase was dried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customThere was obtained a yield of 37.2 g

Sources & evidence

ORD record
ord-c21af86ae2c94abf88a9c0f703b78093
Source dataset
uspto-grants-1977_02
Patent number
US04006154

Reaction notes

Loading…