ethyl imidazo[2,1-b][1,3]benzothiazole-2-carboxylate → (Imidazo[2,1-b][1,3]benzothiazol-2-yl)methanol

HRID 638837Notes

Reaction equation

HRID 638837 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]1[C:8]([C:19](OCC)=[O:20])=[CH:9][N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[S:12][C:11]=12>C1COCC1>[N:7]1[C:8]([CH2:19][OH:20])=[CH:9][N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[S:12][C:11]=12

Participants

4

Reactant 2

HCID 1480574ethyl imidazo[2,1-b][1,3]benzothiazole-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2736621(Imidazo[2,1-b][1,3]benzothiazol-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred slurry of LiAlH4 (2.0 g, excess) in dry THF, ethyl imidazo[2,1-b]-benzthiazole-2-carboxylate (4.9 g, 20 mmol) was slowly added in THF (100 ml) at 0° C. After the addition, the reaction mixture was stirred at room temperature for 1 h and quenched with saturated NH4Cl/NH4OH. The separated solid was diluted with Chloroform/MeOH (3:1) and filtered through a pad of celite. The organic layer was washed once with saturated NaCl and dried over anhydrous MgSO4. It was filtered and concentrated. The brown solid obtained was taken to next step with out purification. Yield: 3.8 g, 93%; M+H 205; mp 131° C.

Workup

  1. additionAfter the addition
  2. customquenched with saturated NH4Cl/NH4OH
  3. additionThe separated solid was diluted with Chloroform/MeOH (3:1)
  4. filtrationfiltered through a pad of celite
  5. washThe organic layer was washed once with saturated NaCl
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationIt was filtered
  8. concentrationconcentrated
  9. customThe brown solid obtained
  10. customwas taken to next step with out purification

Sources & evidence

ORD record
ord-ff51e18a5b32430c83d6930fa1121870
Source dataset
uspto-grants-2010_04
Patent number
US07691842B2

Reaction notes

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