5-(4-chlorophenyl)-1,3,4-oxathiazol-2-one → HCID 90418135, compound

HRID 2177134Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2OC(=O)[S:10][N:9]=2)=[CH:4][CH:3]=1.[F:14][C:15]([F:24])([F:23])[C:16]#[C:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>ClC1C=CC=C(Cl)C=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:16]([C:15]([F:23])([F:24])[F:14])[S:10][N:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Into a 50-mL sealed tube, was placed 5-(4-chlorophenyl)-2H-1,3,4-oxathiazol-2-one (2.2 g, 10.30 mmol, 1.00 equiv), ethyl 4,4,4-trifluorobut-2-ynoate (2.5 g, 15.05 mmol, 1.46 equiv), 1,3-dichlorobenzene (20 mL). The resulting solution was stirred for 18 h at 150° C. in an oil bath. The reaction progress was monitored by LCMS/GCMS/TLC (ethyl acetate/petroleum ether=1:20). The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with petroleum ether. This resulted in 2.8 g (81%) of ethyl 3-(4-chlorophenyl)-5-(trifluoromethyl)-1,2-thiazole-4-carboxylate as a yellow solid. Mass spectrum (ESI, m/z): Calcd. for C13H9ClF3NO2S, 336.0 (M+H). found 336.0.

Workup

customInto a 50-mL sealed tube
concentrationThe resulting mixture was concentrated under vacuum
customThis resulted in 2.8 g (81%) of ethyl 3-(4-chlorophenyl)-5-(trifluoromethyl)-1,2-thiazole-4-carboxylate as a yellow solid

Sources & evidence

ORD record: ord-6574abb55c8348b4aeb276724884f9f1
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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