Hydroxyacetonitrile → N-carboxymethyl-N-cyanomethylamino-2-ethanol

HRID 1740719Notes

Reaction equation

HRID 1740719 reaction equation
[C:1]([CH2:4][NH:5][CH2:6][CH2:7][OH:8])([OH:3])=[O:2].[C:9](#[N:12])[CH2:10]O>>[C:1]([CH2:4][N:5]([CH2:6][CH2:7][OH:8])[CH2:10][C:9]#[N:12])([OH:3])=[O:2]

Participants

3

Reactant 2

HCID 7857HydroxyacetonitrileHCID 225935N-(2-Hydroxyethyl)glycine

Product 1

HCID 11073690N-carboxymethyl-N-cyanomethylamino-2-ethanol

Procedure

The hydrolysis of (I) with base gives N-carboxymethylamino-2-ethanol (II). Compound (II) is then reacted with additional glycolonitrile to form N-carboxymethyl-N-cyanomethylamino-2-ethanol (III). The molar ratio of (II) to glycolonitrile is generally about 1:1. In the above reactions, hydrogen cyanide and formaldehyde can be substituted for glycolonitrile.

Sources & evidence

ORD record
ord-9e6b4a61845a4183a45d4591d3aa95be
Source dataset
uspto-grants-1999_10
Patent number
US05972868

Reaction notes

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