Triethylamine → HCID 531395, compound

HRID 890663Notes

Reaction equation

HRID 890663 reaction equation
Cl.[NH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[C:15]1([C:20](Cl)=[O:21])[S:19][CH:18]=[CH:17][CH:16]=1>ClCCl>[C:15]1([C:20]([NH:2][CH2:3][C:4]([O:6][CH3:7])=[O:5])=[O:21])[S:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 789282-Thiophenecarbonyl chlorideHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 531395HCID 531395, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 250 ml of a suspension of 12.56 g of methyl 2-aminoacetate hydrochloride in dichloromethane, 20.24 g of triethylamine was added, and stirred for 30 minutes at room temperature. After ice-cooling, 20 ml of a solution of 14.66 g of 2-thenoyl chloride in dichloromethane was added dropwise slowly. The ice-bath was removed and the mixture was stirred for 14 hours at room temperature. The precipitated crystals were collected by filtration and washed with dichloromethane. The solvent was removed from the filtrate by distillation under reduced pressure. To the residue was added t-butyl methyl ether to precipitate. The both products were combined to provide 17.20 g of the objective compound as brownish crystals.

Workup

  1. temperatureAfter ice-cooling
  2. customThe ice-bath was removed
  3. stirringthe mixture was stirred for 14 hours at room temperature
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with dichloromethane
  6. customThe solvent was removed from the filtrate by distillation under reduced pressure
  7. additionTo the residue was added t-butyl methyl ether
  8. customto precipitate

Sources & evidence

ORD record
ord-032795d432e34e59b67d60cfe6b17c16
Source dataset
uspto-grants-2006_02
Patent number
US06998412B2

Reaction notes

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