Potassium Hydroxide → (2,4-Dimethoxy-1,3-benzothiazol-7-yl)acetic acid

HRID 963557Notes

Reaction equation

HRID 963557 reaction equation
[CH3:1][O:2][C:3]1[S:4][C:5]2[C:11]([CH2:12][C:13]#N)=[CH:10][CH:9]=[C:8]([O:15][CH3:16])[C:6]=2[N:7]=1.[OH-:17].[K+].C[OH:20].O>>[CH3:1][O:2][C:3]1[S:4][C:5]2[C:11]([CH2:12][C:13]([OH:20])=[O:17])=[CH:10][CH:9]=[C:8]([O:15][CH3:16])[C:6]=2[N:7]=1

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 13814267HCID 13814267, compoundHCID 22242641Methanol--water (1/1)

Product 1

HCID 19082155(2,4-Dimethoxy-1,3-benzothiazol-7-yl)acetic acid

Procedure

A solution of (2,4-dimethoxy-1,3-benzothiazol-7-yl)-acetonitrile (3.61 g, J. Med. Chem., 1987, 30, 1166) and potassium hydroxide (3.45 g) in methanol:water (2:1, 150 ml) was heated to reflux for 6.5 hours. The reaction was cooled and the solvents evaporated under reduced pressure. Water (50 ml) was added and the aqueous layer extracted with diethyl ether. The aqueous layer was then acidified to pH4/5 with acetic acid and extracted with ethyl acetate. The combined organic layers were washed (water and brine), dried (MgSO4) and the solvent evaporated under reduced pressure to yield the subtitled compound which was used in the next step without further purification.

Workup

  1. temperatureto reflux for 6.5 hours
  2. temperatureThe reaction was cooled
  3. customthe solvents evaporated under reduced pressure
  4. additionWater (50 ml) was added
  5. extractionthe aqueous layer extracted with diethyl ether
  6. extractionextracted with ethyl acetate
  7. washThe combined organic layers were washed (water and brine)
  8. dry with materialdried (MgSO4)
  9. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-d309eb177e8647f3840c5d8b77ad7af1
Source dataset
uspto-grants-1998_06
Patent number
US05763465

Reaction notes

Loading…