HCID 90418475, compound → HCID 90418532, compound

HRID 2177237Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([C:14]([O:16][CH2:17]C)=[O:15])=[C:12](S(C)(=O)=O)[S:11][N:10]=2)=[CH:5][CH:4]=1)[CH3:2].[CH3:23][O:24][Na]>CO>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([O:24][CH3:23])[S:11][N:10]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

Into a 100-mL round-bottom flask, was placed a solution of ethyl 3-(4-ethylphenyl)-5-methanesulfonyl-1,2-thiazole-4-carboxylate (150 mg, 0.44 mmol, 1.00 equiv), methanol (15 mL), MeONa (119.47 mg, 5.00 equiv). The resulting solution was stirred for 2 h at 70° C. in an oil bath. The resulting solution was extracted with 2×15 mL of dichloromethane and the organic layers combined. The resulting mixture was washed with 2×30 mL of brine, dried over anhydrous Na2SO4. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 141.4 mg (crude) of methyl 3-(4-ethylphenyl)-5-methoxy-1,2-thiazole-4-carboxylate as white oil. Mass spectrum (ESI, m/z): Calcd. for C15H17NO3S, 292.1 (M+H). found 292.1.

Workup

customInto a 100-mL round-bottom flask, was placed
extractionThe resulting solution was extracted with 2×15 mL of dichloromethane
washThe resulting mixture was washed with 2×30 mL of brine
dry with materialdried over anhydrous Na2SO4
filtrationThe solids were filtered out
concentrationThe resulting mixture was concentrated under vacuum
customThis resulted in 141.4 mg (crude) of methyl 3-(4-ethylphenyl)-5-methoxy-1,2-thiazole-4-carboxylate as white oil

Sources & evidence

ORD record: ord-be32993a10f44c7ba689b8d4226cdfe9
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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