Ethanol → HCID 67041059, compound

HRID 605394Notes

Reaction equation

HRID 605394 reaction equation
S(Cl)(Cl)=O.[NH2:5][C:6]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)([CH3:10])[C:7]([OH:9])=[O:8].[CH2:16](O)[CH3:17]>>[NH2:5][C:6]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)([CH3:10])[C:7]([O:9][CH2:16][CH3:17])=[O:8]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 236333α-Amino-α-methyl-2-thiopheneacetic acid

Product 1

HCID 67041059HCID 67041059, compoundYield 86%

Procedure

Thionyl chloride (1 mL, 14.6 mmol) was added dropwise to 2-amino-2-(thiophen-2-yl)propanoic acid (0.500 g, 2.92 mmol) suspended in anhydrous ethanol (10 mL) at 0° then the reaction was heated at reflux for 22 hours. The reaction was concentrated by rotary evaporation, diluted with water (5 mL), adjusted pH to 9 with 6N aqueous sodium hydroxide, and extracted with ethyl acetate (2×25 mL). The combined organic extracts were washed with brine (25 mL), dried over sodium sulfate, filtered, and concentrated by rotary evaporation to afford the title compound as an oil (0.498 g, 2.499 mmol, 86%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.17 (t, J=7.17 Hz, 3 H) 1.60 (s, 3 H) 2.53 (s, 2 H) 4.11 (q, J=7.23 Hz, 2 H) 6.91-6.98 (m, 1 H) 7.00 (dd, J=3.68, 1.10 Hz, 1 H) 7.37 (dd, J=5.15, 1.10 Hz, 1 H). MS (DCI) m/z 200 (M+H)+, 217 (M+NH4)−.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 22 hours
  3. concentrationThe reaction was concentrated by rotary evaporation
  4. additiondiluted with water (5 mL)
  5. extractionextracted with ethyl acetate (2×25 mL)
  6. washThe combined organic extracts were washed with brine (25 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-b1e7ea15e50a47c79a1db190cb23d33c
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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