Methanol → HCID 68705008, compound

HRID 655231Notes

Reaction equation

HRID 655231 reaction equation
O=S(Cl)Cl.[S:5]1[C:9]2[CH:10]=[C:11]([CH2:14][C:15]([OH:17])=[O:16])[CH:12]=[CH:13][C:8]=2[N:7]=[CH:6]1.[CH3:18]O>>[CH3:18][O:16][C:15](=[O:17])[CH2:14][C:11]1[CH:12]=[CH:13][C:8]2[N:7]=[CH:6][S:5][C:9]=2[CH:10]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 22038417(1,3-Benzothiazol-6-yl)acetic acid

Product 1

HCID 68705008HCID 68705008, compound

Procedure

SOCl2 (13.5 g, 114.0 mmol) was added dropwise to a stirred solution of benzothiazol-6-yl-acetic acid (20.0 g, 103.6 mmol) in 150 ml of methanol at 0° C. under N2. After stirring for 2 hours at room temperature the solvent was evaporated and the residue was diluted with ethyl acetate (150 ml). The mixture was washed with saturated sodium carbonate solution (100 ml×3) and brine (100 ml) and then concentrated in vacuo. The residue was purified by column chromatoghaphy eluting with ethyl acetate/petroleum ether (1:5) to return the title compound as a pale yellow oil (15.0 g, 71.5%).

Workup

  1. customwas evaporated
  2. additionthe residue was diluted with ethyl acetate (150 ml)
  3. washThe mixture was washed with saturated sodium carbonate solution (100 ml×3) and brine (100 ml)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatoghaphy
  6. washeluting with ethyl acetate/petroleum ether (1:5)

Sources & evidence

ORD record
ord-4412a922899a405aa9a99ae8d3e95fc0
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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