Pyridine → Ethyl 2-(2,4,5-trichlorophenyl)oxycarbonyloxyimino-2-cyanoacetate

HRID 1283760Notes

Reaction equation

HRID 1283760 reaction equation
Cl[C:2]([O:4][N:5]=[C:6]([C:12]#[N:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:3].[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[C:18]([Cl:22])=[CH:17][C:16]=1[OH:23].N1C=CC=CC=1>C1C=CC=CC=1>[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[C:18]([Cl:22])=[CH:17][C:16]=1[O:23][C:2]([O:4][N:5]=[C:6]([C:12]#[N:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 72712,4,5-TrichlorophenolHCID 53929971Ethyl 2-chlorocarbonyloxyimino-2-cyanoacetate

Product 1

HCID 54542381Ethyl 2-(2,4,5-trichlorophenyl)oxycarbonyloxyimino-2-cyanoacetateYield 65.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of ethyl 2-chlorocarbonyloxyimino-2-cyanoacetate (0.05 mol) prepared as in Example 11 (1), a solution of 2,4,5-trichlorophenol (9.9 g) and pyridine (3.9 g) in benzene (50 ml) is dropwise added under cooling with icewater. The resulting mixture is stirred for 1 hour and allowed to stand over night. The reaction mixture is washed with water, dried and concentrated. The residue is admixed with petroleum ether and filtered to collect crystals, which is dried and recrystallized from a benzene-petroleum ether mixture to give ethyl 2-(2,4,5-trichlorophenyl)oxycarbonyloxyimino-2-cyanoacetate (12.0 g). M.P. 101 to 103°C.

Workup

  1. temperatureunder cooling with icewater
  2. waitto stand over night
  3. washThe reaction mixture is washed with water
  4. customdried
  5. concentrationconcentrated
  6. filtrationfiltered
  7. customto collect crystals, which
  8. customis dried
  9. customrecrystallized from a benzene-petroleum ether mixture

Sources & evidence

ORD record
ord-f7a2a26cccc8422891c3cb340c4cd9f2
Source dataset
uspto-grants-1976_08
Patent number
US03976635

Reaction notes

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