Water → HCID 14650086, compound

HRID 1722741Notes

Reaction equation

HRID 1722741 reaction equation
[NH2:1][C:2]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)([CH2:7][CH3:8])[C:3]([O:5][CH3:6])=[O:4].[CH2:14](I)[CH3:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C)P(=O)(N(C)C)N(C)C>[CH2:14]([NH:1][C:2]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)([CH2:7][CH3:8])[C:3]([O:5][CH3:6])=[O:4])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 14650085HCID 14650085, compound

Product 1

HCID 14650086HCID 14650086, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

Methyl 2-amino-2-(2-thienyl)butyrate (11.94 g) is dissolved in hexamethylphosphoric triamide (200 ml), and ethyl iodide (28.7 g) and potassium carbonate (37.3 g) is added thereto. The mixture is stirred at room temperature for 4 hours and further stirred at 70° C. for one hour. Water is added to the reaction mixture and the mixture is extracted with ether. The extract is washed with water, dried and concentrated to remove solvent. The residue is purified by silica gel column chromatography, whereby methyl 2-ethylamino-2-(2-thienyl)butyrate (8.99 g) is obtained.

Workup

  1. stirringfurther stirred at 70° C. for one hour
  2. extractionthe mixture is extracted with ether
  3. washThe extract is washed with water
  4. customdried
  5. concentrationconcentrated
  6. customto remove solvent
  7. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a8190cfd5f934a1088b013688f27b11e
Source dataset
uspto-grants-1989_08
Patent number
US04857543

Reaction notes

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