Diethyl Ether → Ethyl N-(thiophene-2-carbonyl)glycinate

HRID 2072676

Reaction equation

HRID 2072676 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].C(=O)([O-])[O-].[K+].[K+].CCOCC.[C:20]1([C:25](Cl)=[O:26])[S:24][CH:23]=[CH:22][CH:21]=1>O.C1C=CC=CC=1>[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH:7][C:25](=[O:26])[C:20]1[S:24][CH:23]=[CH:22][CH:21]=1)[CH3:3]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 789282-Thiophenecarbonyl chlorideHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 1720748Ethyl N-(thiophene-2-carbonyl)glycinateYield 68.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

To a solution of glycine ethyl ester hydrochloride (22 g) and potassium carbonate (86 g) in water (600 ml) was added a mixture of benzene (600 ml) and ether (400 ml) and stirred at room temperature. 2-Thenoyl chloride (25 g) in benzene (100 ml) was added during a period of about 30 minutes under stirring and then the mixture was stirred for 2 hours at room temperature. The organic layer was separated and after dried over anhydrous sodium sulfate, concentrated under reduced pressure to give colorless crystals, which were recrystallized from ethanol to obtain the objective compound (23 g), mp 82°-83° C.

Workup

  1. stirringunder stirring
  2. stirringthe mixture was stirred for 2 hours at room temperature
  3. customThe organic layer was separated
  4. dry with materialafter dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give colorless crystals, which
  7. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-d8668908c7e54640b4194c55a0f5fa75
Source dataset
uspto-grants-1990_04
Patent number
US04914104

Linked notes

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