Chloroacetonitrile → [(5-Chloro-1,3-benzothiazol-2-yl)sulfanyl]acetonitrile

HRID 325977Notes

Reaction equation

HRID 325977 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([SH:10])=[N:7][C:6]=2[CH:11]=1.Cl[CH2:13][C:14]#[N:15].C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10][CH2:13][C:14]#[N:15])=[N:7][C:6]=2[CH:11]=1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 178527796HCID 178527796, compound

Product 1

HCID 13312471[(5-Chloro-1,3-benzothiazol-2-yl)sulfanyl]acetonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

51.0 g (0.254 m), 5-chloro-2-mercaptobenzothiazole, 22.8 g (0.304 m) chloroacetonitrile and 30.7 g triethylamine are dissolved in 600 ml of toluene and the solution is heated to reflux for 3 hr, then allowed to cool to room temperature. The toluene solution is washed with water, dried over anhydrous magnesium sulfate and treated with Darco. After the solvent is removed, the residual solid is recrystallized from 300 ml. benzene. The recovered material is recrystallized from cyclohexane. A total yield of 52 g (86%) is obtained. The recrystallized sample has a melting point of 96°-7° C.

Workup

  1. temperaturethe solution is heated
  2. temperatureto reflux for 3 hr
  3. washThe toluene solution is washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. additiontreated with Darco
  6. customAfter the solvent is removed
  7. customthe residual solid is recrystallized from 300 ml
  8. customThe recovered material is recrystallized from cyclohexane
  9. customA total yield of 52 g (86%) is obtained

Sources & evidence

ORD record
ord-f11a01adcb744535b2e4d99644d3bd84
Source dataset
uspto-grants-1984_04
Patent number
US04443606

Reaction notes

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