Thionyl Chloride → 2-(1-Chloroethyl)-1,3-benzothiazole

HRID 2165073Notes

Reaction equation

HRID 2165073 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10](O)[CH3:11].S(Cl)([Cl:15])=O>C(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([Cl:15])[CH3:11]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 28306741-(1,3-Benzothiazol-2-yl)ethan-1-ol

Product 1

HCID 109979582-(1-Chloroethyl)-1,3-benzothiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-benzothiazolyl)ethanol (2.5 g) prepared according to J. Indian Chem. Soc., 566 (1974) in methylene chloride (50 ml) was added thionyl chloride (3.32 g) and the resulting solution stirred at room temperature for 1 hour. The solution was poured onto ice-water (100 ml) and the organic extract separated. This extract was washed with aqueous bicarbonate (10 ml of a 5% solution) and then with water (50 ml). The methylene chloride layer was dried over anhydrous magnesium sulfate and evaporated to a light yellow oil (2.08 g).

Workup

  1. additionThe solution was poured onto ice-water (100 ml)
  2. extractionthe organic extract
  3. customseparated
  4. washThis extract was washed with aqueous bicarbonate (10 ml of a 5% solution) and then with water (50 ml)
  5. dry with materialThe methylene chloride layer was dried over anhydrous magnesium sulfate
  6. customevaporated to a light yellow oil (2.08 g)

Sources & evidence

ORD record
ord-b7ea343a2c8946b4a3ba7c2e6a332844
Source dataset
uspto-grants-1990_07
Patent number
US04939140

Reaction notes

Loading…