Potassium Carbonate → 2-methyl-5-[[(2S)-oxiran-2-yl]methoxy]-1,3-benzothiazole

HRID 891048Notes

Reaction equation

HRID 891048 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:5]=2[N:6]=1.[CH2:12]([C@H:14]1[O:16][CH2:15]1)Cl.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:16]1[CH2:15][C@H:14]1[CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:4]2[S:3][C:2]([CH3:1])=[N:6][C:5]=2[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 149428(+)-EpichlorohydrinHCID 6997992-Methyl-1,3-benzothiazol-5-ol

Product 1

HCID 235989442-methyl-5-[[(2S)-oxiran-2-yl]methoxy]-1,3-benzothiazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-methylbenzothiazol-5-ol, a compound of formula (1) (6.0 g, 36 mmol), (S)-(+)-epichlorohydrin, a compound of formula (2) (20 ml, 182 mmol), and potassium carbonate (20 g, 144 mmol) in acetone (100 ml), was heated to reflux and allowed to stir overnight. The solution was allowed to cool and filtered through Celite 512. The filtrate was evaporated (in vacuo), to yield an oil. The oil was chromatographed on silica gel, eluting with 20% ethyl acetate/hexanes, to yield 5-[((2S)oxiran-2-yl)methoxy]-2-methylbenzothiazole as a white solid (6.2 g, 28 mmol).

Workup

  1. temperatureto reflux
  2. temperatureto cool
  3. filtrationfiltered through Celite 512
  4. customThe filtrate was evaporated (in vacuo)
  5. customto yield an oil
  6. customThe oil was chromatographed on silica gel
  7. washeluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c42b9e007ad0443caf89cf0da1aa6a29
Source dataset
uspto-grants-2006_02
Patent number
US07001909B2

Reaction notes

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