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Ammonia → Ethyl 4-isopropylthiazole-2-carboxylate

HRID 530708
Notes
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Reaction equation

HRID 530708 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 108990371-Bromo-3-methylbutan-2-oneHCID 86627749Ethylthioxamate

Product 1

HCID 10821861Ethyl 4-isopropylthiazole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 962
Water
Solvent

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

  1. extractionThe aqueous layer was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customremoved under reduced pressure
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes