Ammonia → Ethyl 4-isopropylthiazole-2-carboxylate

HRID 530708Notes

Reaction equation

Br[CH2:2][C:3](=O)[CH:4]([CH3:6])[CH3:5].C(OC(C1O[S:15]C=CC=1)=O)C.[NH3:19].[CH3:20][CH2:21][O:22][C:23]([CH3:25])=[O:24]>C(O)C.O>[CH:4]([C:3]1[N:19]=[C:25]([C:23]([O:22][CH2:21][CH3:20])=[O:24])[S:15][CH:2]=1)([CH3:6])[CH3:5]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of compound 211 (3.5 g, 1.25 eq.) and ethylthioxamate (2.3 g, 1 eq.) in ethanol (40 mL) was heated to 80° C. for 6 hrs, and then cooled to 0° C. The reaction mixture was diluted with water and EtOAc, and then neutralized to pH 7 with NH3 (28%). The aqueous layer was extracted with EtOAc. The combined organic layers were dried over sodium sulfate and then removed under reduced pressure. The residue was purified by chromatography on silica gel to yield compound 212 as yellow oil in quantitative yield. 1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.25 (d, J=6.73 Hz, 6H), 1.31 (t, J=7.24 Hz, 3H), 3.11 (hep, J=6.73 Hz, 1H), 4.35 (q, J=7.24 Hz, 2H), 7.72 (s, 1H).

Workup

extractionThe aqueous layer was extracted with EtOAc
dry with materialThe combined organic layers were dried over sodium sulfate
customremoved under reduced pressure
customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-e39a9cfbf9624208905a78363d0539be
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353100B2

Reaction notes

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