Furfurylamine → Ethyl 2-{[(furan-2-yl)methyl]amino}acetate
Reaction equation
[CH2:1]([NH2:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>O1CCCC1>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][NH:7][CH2:1][C:2]1[O:6][CH:5]=[CH:4][CH:3]=1)[CH3:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Furfurylamine (48.6 g, 0.5 mol) and triethylamine (50.6 g, 0.5 mol) were dissolved in tetrahydrofuran (1000 mL) and cooled to 0°-5° C. with an ice water bath. Ethyl chloroacetate (61.3 g, 0.5 mol) was dropwise added at 0°-5° C. to the solution. After addition the mixture was allowed to warm up to room temperature and then stirred over night. The precipitated white triethylamine hydrochloride was filtered off and the filtrate concentrated to an oil which was dissolved in ether and cooled by means of an ice water bath. Ether which has been saturated with dry hydrogen chloride was added to the solution whereby the HCl salt of the product precipitated first as a sticky semisolid. Repeated treatment with anhydrous ether afforded the desired product. Filtration yielded 48.4 g product as an amber solid. Used as is for further synthesis.
Workup
- temperaturecooled to 0°-5° C. with an ice water bath
- additionAfter addition the mixture
- filtrationThe precipitated white triethylamine hydrochloride was filtered off
- concentrationthe filtrate concentrated to an oil which
- dissolutionwas dissolved in ether
- temperaturecooled by means of an ice water bath
- additionwas added to the solution whereby the HCl salt of the product
- customprecipitated first as a sticky semisolid
Sources & evidence
- ORD record
- ord-016d2938320d4519a19f50669f27ba80
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05221665
Reaction notes
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