Ethyl vinyl ether → HCID 57434727, compound

HRID 1363068Notes

Reaction equation

HRID 1363068 reaction equation
[Br:1][C:2]1[C:6]([CH:7]=[O:8])=[C:5]([Br:9])[NH:4][N:3]=1.[CH:10]([O:12][CH2:13][CH3:14])=[CH2:11]>Cl.C1(C)C=CC=CC=1>[Br:1][C:2]1[C:6]([CH:7]=[O:8])=[C:5]([Br:9])[N:4]([CH:10]([O:12][CH2:13][CH3:14])[CH3:11])[N:3]=1

Participants

5

Reactant 2

HCID 8023Ethyl vinyl ether2×HCID 574347263,5-dibromo-1H-pyrazole-4-carbaldehyde

Product 1

HCID 57434727HCID 57434727, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 1140TolueneSolvent2×

Procedure

1 g (3.94 mmol) of 3,5-dibromo-1H-pyrazole-4-carboxaldehyde, 1.5 cm3 (16 mmol) of ethyl vinyl ether and 3 drops of 12N concentrated hydrochloric acid are introduced with stirring into 30 cm3 of toluene at a temperature in the region of 20° C. The reaction mixture is stirred for 15 hours at a temperature in the region of 20° C., 1.5 cm3 (16 mmol) of ethyl vinyl ether are then run in and stirring is continued for 15 hours at a temperature in the region of 20° C. The reaction mixture is then diluted with 20 cm3 of toluene and washed with twice 30 cm3 of saturated sodium hydrogen carbonate solution. The organic phase is dried over magnesium sulfate and concentrated to dryness under reduced pressure (2.7 kPa) to give 1.19 g of 3,5-dibromo-1-(1-ethoxyethyl)-1H-pyrazole-4-carboxaldehyde in the form of a yellow oil. 1H NMR spectrum (300 MHz, (CD3)2SO-d6, δ in ppm): 1.10 (t, J=7.5 Hz: 3H); 1.64 (d, J=6.5 Hz: 3H); 3.31 (mt: 1H); 3.51 (mt: 1H); 5.88 (q, J=6.5 Hz: 1H); 9.73 (s: 1H).

Workup

  1. washwashed with twice 30 cm3 of saturated sodium hydrogen carbonate solution
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-993ad3cbdd0543e9a06d82fa79efb56b
Source dataset
uspto-grants-2011_02
Patent number
US07884123B2

Reaction notes

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