Hydrochloric Acid → 2-[(Azetidin-3-yloxy)methyl]-1,3-thiazole hydrochloride

HRID 82953Notes

Reaction equation

HRID 82953 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][O:7][CH:8]1[CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]1.[ClH:19]>C(OCC)C>[ClH:19].[NH:10]1[CH2:11][CH:8]([O:7][CH2:6][C:2]2[S:1][CH:5]=[CH:4][N:3]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67154588Tert-butyl 3-(1,3-thiazol-2-ylmethoxy)azetidine-1-carboxylate

Product 1

HCID 671544802-[(Azetidin-3-yloxy)methyl]-1,3-thiazole hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of tert-butyl 3-(1,3-thiazol-2-ylmethoxy)azetidine-1-carboxylate (193 mg, 0.71 mmol; which may be prepared as described in Step 2) dissolved in diethyl ether (2.6 mL) at room temperature was added HCl 2N in diethyl ether (7.1 mL). The reaction mixture was stirred for 1.5 h then concentrated to dryness. The resulting solid was triturated with diethyl ether, collected and dried to give the title compound (138 mg, quantitative) as a brown oil.

Workup

  1. concentrationthen concentrated to dryness
  2. customThe resulting solid was triturated with diethyl ether
  3. customcollected
  4. customdried

Sources & evidence

ORD record
ord-d5ebb23cd03a4df6810aac6d2afaf3d9
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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