Potassium Hydroxide → HCID 19082155, compound

HRID 265291Notes

Reaction equation

HRID 265291 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 19082155HCID 19082155, compound

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 refluxed for 61/2 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 ethereal layer was discarded). The aqueous layer was acidified with acetic acid to pH 4/5 and this was extracted several times with ethyl acetate. These combined organic extracts were washed with water and brine, dried (MgSO4) and the solvent evaporated under reduced pressure to yield the crude subtitled compound, (2.978 g) which was used in step b) without further purification.

Workup

  1. temperatureThe reaction was cooled
  2. customthe solvents evaporated under reduced pressure
  3. additionWater (50 ml) was added
  4. extractionthe aqueous layer extracted with diethyl ether (the ethereal layer
  5. extractionthis was extracted several times with ethyl acetate
  6. washThese combined organic extracts were washed with water and brine
  7. dry with materialdried (MgSO4)
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-9a4d62a44a354d69ab58eceb6ff69429
Source dataset
uspto-grants-1997_07
Patent number
US05648370

Reaction notes

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