Hydrochloric Acid → Methyl 2-cyano-2-ethoxyiminoacetate

HRID 647110Notes

Reaction equation

HRID 647110 reaction equation
[C:1]([C:4](=[N:9][O:10][CH2:11][CH3:12])[C:5]([O:7][CH3:8])=[O:6])(=O)[NH2:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(OC(C)C)(C)C.Cl>N1C=CC=CC=1.O>[C:1]([C:4](=[N:9][O:10][CH2:11][CH3:12])[C:5]([O:7][CH3:8])=[O:6])#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 9845Trifluoroacetic anhydrideHCID 53690437Methyl 3-amino-2-(ethoxyimino)-3-oxopropanoate

Product 1

HCID 53675257Methyl 2-cyano-2-ethoxyiminoacetateYield 90.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of methyl 2-carbamoyl-2-ethoxyiminoacetate (syn isomer) (5.22 g) in pyridine (50 ml) was dropwise added trifluoroacetic anhydride (15.7 g) below 25° C. under cooling in an ice-bath and stirring, which was continued for 30 minutes. The reaction mixture was poured into water (200 ml), followed by an addition of diisopropyl ether (200 ml). The mixture was adjusted to pH 2 with 6 N hydrochloric acid (80 ml) at 15° to 20° C. and the organic layer was separated out, washed with water, dried over magnesium sulfate and evaporated to give methyl 2-cyano-2-ethoxyiminoacetate (syn isomer) (4.23 g) as an oil.

Workup

  1. temperatureunder cooling in an ice-bath
  2. customthe organic layer was separated out
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-13b17d3aa9324f2faf70afbbe582d7d5
Source dataset
uspto-grants-1983_10
Patent number
US04407798

Reaction notes

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