Ethanol → 2-(5-Acetyl-thiophen-2-ylmethyl)-thiazole-4-carboxylic acid ethyl ester

HRID 1189419Notes

Reaction equation

HRID 1189419 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[S:13][C:12]([CH2:14][C:15]([NH2:17])=[S:16])=[CH:11][CH:10]=2)[O:8]CCO1.C([CH:20](Br)[C:21](=O)[C:22]([O-:24])=[O:23])C.[CH2:27](O)[CH3:28]>>[CH2:27]([O:24][C:22]([C:21]1[N:17]=[C:15]([CH2:14][C:12]2[S:13][C:9]([C:4](=[O:8])[CH3:3])=[CH:10][CH:11]=2)[S:16][CH:20]=1)=[O:23])[CH3:28]

Participants

5

Reactant 4

HCID 702EthanolHCID 947NitrogenHCID 21948992EthylbromopyruvateHCID 866649192-[5-(2-Methyl-[1,3]dioxolan-2-yl)-thiophen-2-yl]-thioacetamide

Product 1

HCID 671284092-(5-Acetyl-thiophen-2-ylmethyl)-thiazole-4-carboxylic acid ethyl ester

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-[5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-2-yl]-thioacetamide (2.88 g, 11.83 mmol) and ethylbromopyruvate (1.74 mL, 11.83 mmol) in ethanol (34.0 mL) was stirred for 16 h at reflux. The solvent was removed under reduced pressure and the residue was dissolved in EA (150 mL) and washed with 7% aq. NaHCO3 (100 mL). The org. phase was dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (1:1 hept-EA) gave the title compound as an orange oil. TLC: rf (1:1 hept-EA)=0.24. LC-MS-conditions 02: tR=0.93 min, [M+H]+=296.37.

Workup

  1. temperatureat reflux
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in EA (150 mL)
  4. washwashed with 7% aq. NaHCO3 (100 mL)
  5. dry with materialphase was dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customPurification of the residue by FC (1:1 hept-EA)

Sources & evidence

ORD record
ord-d527db5193b14655bb03d0a7e269a7a0
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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