2-Chloro-6-methoxybenzothiazole → HCID 131730290, compound

HRID 1944652Notes

Reaction equation

HRID 1944652 reaction equation
[Cl:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:13]1([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:15][CH2:14]1>C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[ClH:1].[CH:13]1([N:16]2[CH2:21][CH2:20][N:19]([C:2]3[S:3][C:4]4[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=4[N:6]=3)[CH2:18][CH2:17]2)[CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 2731322-Chloro-6-methoxybenzothiazoleHCID 47420041-Cyclopropylpiperazine

Product 1

HCID 131730290HCID 131730290, compoundYield 18.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-chloro-6-methoxybenzothiazole (0.20 g, 1.0 mmol) and 1-cyclopropyl-piperazine (0.25 g, 2.0 mmol) was stirred at 120° C. overnight. The reaction mixture was allowed to cool and dissolved in a mixture of ethyl acetate a NaHCO3 solution. The phases were separated and the organic phase was washed with water (3×) and then extracted with 0.25 M hydrochloric acid (20 mL). The acidic aqueous extract was concentrated and re-evaporated with ethanol. The residue was crystallized from a mixture of ethanol and ethyl acetate to give 60 mg (18%) of 2-(4-cyclopropylpiperazin-1-yl)-6-methoxybenzothiazole, hydrochloride.

Workup

  1. temperatureto cool
  2. customThe phases were separated
  3. washthe organic phase was washed with water (3×)
  4. extractionextracted with 0.25 M hydrochloric acid (20 mL)
  5. extractionThe acidic aqueous extract
  6. concentrationwas concentrated
  7. customre-evaporated with ethanol
  8. customThe residue was crystallized from a mixture of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-2c9967c6d67446d6b7e20f9b7cfeec33
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

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