2-Amino-1-butanol → 2-Amino-1-butanol

HRID 267840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 267840
[Cl:1][CH2:2][CH:3]([N:6]=[C:7]([Cl:9])[CH3:8])[CH2:4][CH3:5].[Cl:10][CH2:11][CH:12]([N:15]=[C:16](Cl)[CH3:17])[CH2:13][CH3:14].O.[CH3:20][CH2:21][CH:22]([NH2:25])[CH2:23][OH:24].[OH:26]CC(NC(=O)C)CC>C(O)C.CO.C(O)(=O)C>[CH3:20][CH2:21][CH:22]([NH2:25])[CH2:23][OH:24].[Cl:1][CH2:2][CH:3]([N:6]=[C:7]([Cl:9])[CH3:8])[CH2:4][CH3:5].[Cl:10][CH2:11][CH:12]([NH:15][C:16](=[O:26])[CH3:17])[CH2:13][CH3:14]

Komponenten

10

Edukt 4

HCID 221292-Amino-1-butanolHCID 249903N-(1-hydroxybutan-2-yl)acetamideHCID 12803236(1E)-N-(1-Chlorobutan-2-yl)ethanimidoyl chlorideHCID 86733162water N-[1-(chloromethyl)propyl]acetimidoyl chloride

Produkt 3

HCID 221292-Amino-1-butanolHCID 12803236(1E)-N-(1-Chlorobutan-2-yl)ethanimidoyl chlorideHCID 12803237N-(1-Chlorobutan-2-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

Hydrolysis of N-[1-(chloromethyl)propyl]acetimidoyl chloride is highly pH dependent. It has now been found that a simple hydrolysis procedure is effective. On refluxing with water N-[1-(chloromethyl)propyl]acetimidoyl chloride is transformed into a mixture of dl-2-amino-1-butanol (77%), dl-2-amino-1-butanol acetate hydrochloride (17%), the N-[1-(hydroxymethyl)propyl]acetamide (7%) and acetic acid within one hour. The product ratios appear to represent equilibrium compositions because additional heating (14 hrs.) does not materially change their distribution. If, however, the hydrolysis is carried out with aqueous methanol or ethanol, it is complete within 2 hours and the acetyl component of the product can be removed as methyl or ethyl acetate by distillation. This procedure not only decreases hydrolysis time, it also avoids the accumulation of salts in the reaction mixture, gives essentially quantitative yields of dl-2-amino-1-butanol from N-[1-(chloromethyl)propyl]acetimidoyl chloride through N-[1-(chloromethyl)propyl]acetamide, and facilitates product work-up. Methyl acetate boils at 57° C., and is readily distilled off.

Aufarbeitung

  1. customIt has now been found that a simple hydrolysis procedure
  2. temperaturebecause additional heating (14 hrs.)
  3. customthe acetyl component of the product can be removed as methyl or ethyl acetate by distillation
  4. customThis procedure not only decreases hydrolysis time, it
  5. customgives essentially quantitative

Quellen und Nachweise

ORD-Eintrag
ord-5d04832110574de6a2000b50005625ff
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03944608

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