21224-20-4 → Methyl 5-(1,3-benzothiazol-2-yl)pentanoate

HRID 478738Notes

Reaction equation

HRID 478738 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15].Cl.[CH3:18]O>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:18])=[O:15]

Participants

3

Reactant 2

HCID 197149321224-20-4HCID 21893726Hydrochloride methanol

Product 1

HCID 18002644Methyl 5-(1,3-benzothiazol-2-yl)pentanoateYield 67%

Procedure

A solution of 5-(2-benzothiazolyl)pentanoic acid (1.54 g, 6.5 mmol, prepared according to the procedure of Example 12 in JP, A, 8-208631 (1996)) in hydrochloric acid-methanol (40 ml) was stirred at room temperature overnight, and evaporated. The residue was dissolved in chloroform, and washed with saturated aqueous sodium hydrogen carbonate. The organic layer was dried over anhydrous magnesium sulfate, evaporated, and purified through flash column chromatography to give methyl 5-(2-benzothiazolyl)pentanoate (1.08 g, 67%).

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed with saturated aqueous sodium hydrogen carbonate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customevaporated
  6. custompurified through flash column chromatography

Sources & evidence

ORD record
ord-6ea897a685174315ac633287610bf07e
Source dataset
uspto-grants-2003_11
Patent number
US06642250B2

Reaction notes

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