Potassium Carbonate → 2-(5-Chloropentyloxy)benzo[d]thiazole

HRID 1911913Notes

Reaction equation

HRID 1911913 reaction equation
[OH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][Cl:23]>C(#N)C.CCOC(C)=O>[Cl:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][O:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 960701-Bromo-5-chloropentaneHCID 178517143HCID 178517143, compound2×

Product 1

HCID 715295852-(5-Chloropentyloxy)benzo[d]thiazole

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-hydroxybenzothiazole (0.2 g, 1.32 mmol) in 10 mL of acetonitrile was added K2CO3 (0.274 g, 1.98 mmol), followed by stirring at 50˜55° C. for 30 min. Then, 1-bromo-5-chloropentane (0.245 g, 1.32 mmol) was added to and reacted with the solution of 2-hydroxybenzothiazole at 80˜90° C. for 3 hours. The reaction was cooled to room temperature, diluted with 10 mL of EtOAc, and washed with distilled water and a saturated NaCl aqueous solution. It was dried over MgSO4 and the solvent was removed by concentration under reduced pressure to afford K23 (0.333 g, 98%).

Workup

  1. washwashed with distilled water
  2. dry with materialIt was dried over MgSO4
  3. customthe solvent was removed by concentration under reduced pressure
  4. customto afford K23 (0.333 g, 98%)

Sources & evidence

ORD record
ord-5c9542e12e5648b8b7309b1726867a5b
Source dataset
uspto-grants-2013_12
Patent number
US08604214B2

Reaction notes

Loading…