Triethanolamine → Ethyl (2-cyanoaziridin-1-yl)acetate

HRID 2059006Notes

Reaction equation

HRID 2059006 reaction equation
Cl.Br[CH:3]([CH2:6][NH:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]#[N:5].N(CCO)(CCO)CCO>>[C:4]([CH:3]1[CH2:6][N:7]1[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])#[N:5]

Participants

3

Reactant 2

HCID 7618TriethanolamineHCID 20483660HCID 20483660, compound

Product 1

HCID 20483606Ethyl (2-cyanoaziridin-1-yl)acetateYield 34%

Procedure

reaction of 2-bromo-3-(carbethoxymethylamino)-propionitrile hydrochloride (prepared by reacting 2,3-dibromopropionitrile with glycine ethyl ester; m.p. 70°-75° C.) with triethanolamine gives ethyl 2-cyano-1-aziridineacetate; b.p.0.1 : 88°-90° C.; yield 34% of theory;

Sources & evidence

ORD record
ord-75f3402201324efcb96ac1779725469a
Source dataset
uspto-grants-1982_03
Patent number
US04321194

Reaction notes

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