Phenol → HCID 54226967, compound

HRID 1905403Notes

Reaction equation

HRID 1905403 reaction equation
[CH3:1][N:2]1[C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:5]([CH:14]=[N:15][O:16][CH2:17][C:18]2[CH:26]=[CH:25][C:21]([C:22](O)=O)=CC=2)[C:4]([CH3:27])=[N:3]1.[C:28]1([OH:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=N[C:56](OCC)=[O:57]>CCOCC>[CH3:1][N:2]1[C:6]([O:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[C:5]([CH:14]=[N:15][O:16][C:17]2[CH:18]=[CH:26][C:25]([C:56]([O:34][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:57])=[CH:21][CH:22]=2)[C:4]([CH3:27])=[N:3]1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 545462834-[[(Z)-(1,3-Dimethyl-5-phenoxypyrazol-4-yl)methylideneamino]oxymethyl]benzoic acid

Product 1

HCID 54226967HCID 54226967, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.0 Gram (0.0027 mole) of 4-[(1,3-dimethyl-5-phenoxypyrazol-4-yl)methyleneaminooxymethyl]benzoic acid, 0.25 g (0.0027 mole) of phenol and 0.7 g (0.0027 mole) of triphenylphosphine were added to 50 ml of ether, and the resulting mixture was stirred. To this solution was added 0.47 g (0.0027 mole) of diethyl azodicarboxylate, and the resulting solution was heated under reflux for 3 hours. After completion of the reaction, the ether layer was filtered, and ether was removed by evaporation to obtain an oily product. This oily product was column-chromatographed on silica gel to obtain 0.9 g of the desired compound.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 3 hours
  3. customAfter completion of the reaction
  4. filtrationthe ether layer was filtered
  5. customether was removed by evaporation
  6. customto obtain an oily product
  7. customThis oily product was column-chromatographed on silica gel

Sources & evidence

ORD record
ord-bdc50c1fdf4645f0b591e3a84dcd780c
Source dataset
uspto-grants-1989_06
Patent number
US04843068

Reaction notes

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