Triethylamine → HCID 20232064, compound

HRID 2290376Notes

Reaction equation

HRID 2290376 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][CH:10]([CH3:18])[C:11]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)=[O:12].Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(Cl)(Cl)Cl>[CH2:23]([O:22][C:20]([NH:9][CH:10]([CH3:18])[C:11]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)=[O:12])=[O:21])[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 70448803HCID 70448803, compound

Product 1

HCID 20232064HCID 20232064, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A solution of triethylamine (5.455 g) in chloroform (5 ml) was added dropwise to a stirred solution of 2-amino-1-(2-thienyl)-1-propanone hydrochloride (2.585 g) in chloroform (26 ml) under ice cooling in 5 minutes. To the mixture was added dropwise a solution of ethyl chloroformate (2.929 g) in chloroform (7 ml), and the stirring was continued for 2 hours under the same conditions. The reaction mixture was evaporated, and the residue was dissolved in a mixture of ethyl acetate and water. The organic layer was separated, washed successively with a saturated aqueous solution of sodium bicarbonate, water, 5% hydrochloric acid and water, dried over magnesium sulfate and evaporated to give an oil of 2-(2-ethoxycarbonylaminopropionyl)thiophene (2.752 g).

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed successively with a saturated aqueous solution of sodium bicarbonate, water, 5% hydrochloric acid and water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-8f1b4951cec445289f1be392ca21a204
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

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