Phosgene → Ethyl 2-chlorocarbonyloxyimino-2-cyanoacetate

HRID 1283759Notes

Reaction equation

HRID 1283759 reaction equation
[OH:1][N:2]=[C:3]([C:9]#[N:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(N(CC)CC)C.[C:18](Cl)([Cl:20])=[O:19]>C1C=CC=CC=1>[Cl:20][C:18]([O:1][N:2]=[C:3]([C:9]#[N:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:19]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetate

Product 1

HCID 53929971Ethyl 2-chlorocarbonyloxyimino-2-cyanoacetate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

In dry benzene (50 ml), ethyl 2-hydroxyimino-2-cyanoacetate (7.2 g) and triethylamine (7.0 ml) are dissolved, and the resulting solution is dropwise added to a solution of phosgene (0.05 mol) in benzene (52.5 ml) at 5°C. The mixture is stirred at the same temperature for 2 hours and allowed to stand at room temmperature over night to give a solution of ethyl 2-chlorocarbonyloxyimino-2-cyanoacetate.

Workup

  1. waitto stand at room temmperature over night

Sources & evidence

ORD record
ord-8450049bf4864cfaab28735617804860
Source dataset
uspto-grants-1976_08
Patent number
US03976635

Reaction notes

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