Triethylamine → 5-(Azetidine-1-sulfonyl)-2-chloro-4-methyl-1,3-thiazole

HRID 1990284Notes

Reaction equation

[Cl:1][C:2]1[S:3][C:4]([S:8](Cl)(=[O:10])=[O:9])=[C:5]([CH3:7])[N:6]=1.Cl.[NH:13]1[CH2:16][CH2:15][CH2:14]1.C(N(CC)CC)C>C(Cl)Cl>[N:13]1([S:8]([C:4]2[S:3][C:2]([Cl:1])=[N:6][C:5]=2[CH3:7])(=[O:10])=[O:9])[CH2:16][CH2:15][CH2:14]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-chloro-4-methylthiazole-5-sulphonylchloride (462 mg; 2.0 mmol) in DCM (5 mL) was added to an ice-cold solution of azetidine hydrochloride (196 mg; 2.1 mmol) and triethylamine (1.0 mL; 7.2 mmol) in DCM (15 mL) and the mixture stirred at 0° C. for 30 minutes. The DCM was removed in vacuo to give a residue which was partitioned between water (50 mL) and ethyl acetate (75 mL). The organic layer was washed with brine, dried (MgSO4) and evaporated to a residue which was chromatographed on silica, eluting with 10% ethyl acetate in isohexane, to give the desired material as a solid which was crystallised from ethyl acetate and isohexane (100 mg).

Workup

customThe DCM was removed in vacuo
customto give a residue which
customwas partitioned between water (50 mL) and ethyl acetate (75 mL)
washThe organic layer was washed with brine
dry with materialdried (MgSO4)
customevaporated to a residue which
customwas chromatographed on silica
washeluting with 10% ethyl acetate in isohexane

Sources & evidence

ORD record: ord-4b0fef404ee14d55901907f7dfe51a40
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642259B2

Reaction notes

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