Hydrochloric Acid → 1-(4,5-Dihydrothiazol-2-yl)azetidin-3-ol

HRID 1957374Notes

Reaction equation

HRID 1957374 reaction equation
[OH:1][CH:2]1[CH2:5][NH:4][CH2:3]1.Cl.C[C:8]1[S:9][CH2:10][CH2:11][N:12]=1.C[O-].[Na+]>C(O)C>[OH:1][CH:2]1[CH2:5][N:4]([C:8]2[S:9][CH2:10][CH2:11][N:12]=2)[CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 16867Thiazole, 4,5-dihydro-2-methyl-2×HCID 15142903-HydroxyazetidineHCID 10942334Sodium Methoxide

Product 1

HCID 109865151-(4,5-Dihydrothiazol-2-yl)azetidin-3-olYield 81.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 109 mg of 3-hydroxyazetidine.HCl [Compound (1)] in 5 ml of ethanol was added a mixture of 133 mg of 2-methylthiazoline [Compound (2)] and sodium methoxide, and the reaction mixture was refluxed for 8 hours. After removal of the solvent under reduced pressure, the resulting residue was dissolved in chloroform and washed with 50% aqueous potassium carbonate solution. The solvent was removed under reduced pressure to give 119 mg (81.5%) of 3-hydroxy-1-(thiazolin-2-yl)azetidine [Compound (3)] as a crystaline.

Workup

  1. temperaturethe reaction mixture was refluxed for 8 hours
  2. customAfter removal of the solvent under reduced pressure
  3. dissolutionthe resulting residue was dissolved in chloroform
  4. washwashed with 50% aqueous potassium carbonate solution
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-df0909faa5fa4ec9a3fb619931707162
Source dataset
uspto-grants-1998_07
Patent number
US05783703

Reaction notes

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