1-Bromo-3-chloropropane → 2-Methyl-5-(3-chloropropoxyl)-benzothiazole

HRID 1016493Notes

Reaction equation

HRID 1016493 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:5]=2[N:6]=1.Br[CH2:13][CH2:14][CH2:15][Cl:16].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH2:13][CH2:14][CH2:15][Cl:16])=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 6997992-Methyl-1,3-benzothiazol-5-ol

Product 1

HCID 184070592-Methyl-5-(3-chloropropoxyl)-benzothiazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-methyl-5-benzothiazolol (8 g, 48.4 mmol), 1-bromo-3-chloropropane (23 g, 146 mmol), and potassium carbonate (33.6 g, 240 mmol) in 50 ml of acetonitrile was stirred at 60° C. for 18 hr. The mixture was cooled, evaporated under reduced pressure, diluted with water and ethyl acetate. The organic phase was separated, dried over sodium sulfate, and concentrated under vacuum to give 2-methyl-5-(3-chloropropoxyl)-benzothiazole (IV) as a tan crystalline solid (10 g, 85%, mp 63-65° C., MS (CI) m+1=242).

Workup

  1. temperatureThe mixture was cooled
  2. customevaporated under reduced pressure
  3. additiondiluted with water and ethyl acetate
  4. customThe organic phase was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7c016034292f4955bb7f95a3a91c8a26
Source dataset
uspto-grants-2002_11
Patent number
US06476051B2

Reaction notes

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