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

HRID 1835

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

Reactant 2

HCID 7857Hydroxyacetonitrile

HCID 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-2bfdd368208a447a97e7268f9780631d
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05726341

Linked notes

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