Hydrochloric Acid → HCID 67933391, compound

HRID 1088444Notes

Reaction equation

HRID 1088444 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]([C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)=[O:6].[C:12](OC(=O)C)(=[O:14])[CH3:13].[C:19]([O-])(=[O:21])C.[Na+].[C:24]([NH:27][CH2:28][C:29]([C:31]1[O:32][CH:33]=[CH:34][CH:35]=1)=[O:30])(=[O:26])[CH3:25].C=O.C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[O:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[CH:5]([OH:6])[CH:4]([C:19]([CH:28]([NH:27][C:24](=[O:26])[CH3:25])[CH:29]([OH:30])[C:31]1[O:32][CH:33]=[CH:34][CH:35]=1)=[O:21])[NH:3][C:12](=[O:14])[CH3:13]

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 132261382-Amino-1-(furan-2-yl)ethan-1-one--hydrogen chloride (1/1)HCID 13773126N-[2-(Furan-2-yl)-2-oxoethyl]acetamide

Product 1

HCID 67933391HCID 67933391, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

U.S. Patent 2,547,712 describes a process for producing certain 1-[2-furyl]-2-aminopropane diols. In a more relevant disclosure, in Example 2 of the '712 patent, the compound 2-furyl aminomethyl ketone hydrochloride is produced by reacting a 2-furyl bromomethyl ketone hexamethylene tetraamine complex with HCl. In the next step the 2-furyl aminomethyl ketone is added to a mixture of glacial acetic acid and acetic anhydride to which is then added sodium acetate. The product of that reaction is 2-furyl acetamidomethyl ketone, which is reacted with formalin, sodium bicarbonate and methanol to form 2-furyl-α-acetamido-β-hydroxyethyl ketone. This product was then reduced to the corresponding diol with aluminum isopropoxide (the catalyst of the '913 patent) in isopropanol.

Sources & evidence

ORD record
ord-d111ea77243242aeae3ec463bdb8dd68
Source dataset
uspto-grants-1990_10
Patent number
US04962212

Reaction notes

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