Hydrochloric Acid → HCID 19786944, compound

HRID 1657026Notes

Reaction equation

HRID 1657026 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:8]=2)[CH:5]=[N:4][C:3]=1[CH:20]=[N:21][OH:22].Cl.BrN1C(=O)CCC1=O.[CH2:32]([O:35][CH3:36])[C:33]#[CH:34]>CN(C)C=O.C(N(CC)CC)C>[CH3:36][O:35][CH2:32][C:33]1[O:22][N:21]=[C:20]([C:3]2[N:4]=[CH:5][N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:8]=3)[C:2]=2[CH3:1])[CH:34]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 67184N-bromobutanimide2×HCID 693933-MethoxypropyneHCID 53939519HCID 53939519, compound

Product 1

HCID 19786944HCID 19786944, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8471TriethylamineSolvent3×

Procedure

660 mg of 5-methyl-1-(3-phenoxyphenyl)-imidazole-4-carbaldehydoxime, hydrochloride is dissolved in 4 ml of dimethylformamide. At 0° C., 0.28 ml of triethylamine is added and a solution of 360 mg of N-bromosuccinimide in 2 ml of dimethylformamide is instilled within one hour. Then, 1.7 ml of methyl propargyl ether and 0.28 ml of triethylamine are added, and the mixture is stirred for 14 hours at room temperature. 360 mg of N-bromosuccinimide in 2 ml of dimethylformamide and 0.28 ml of triethylamine are again added and the mixture is stirred for 18 hours at room temperature. After the concentration by evaporation, it is mixed with water and extracted with ethyl acetate. The extract that has been concentrated by evaporation is mixed with diethyl ether and filtered. The filtrate is purified by column chromatography. 230 mg (32% of theory) of the title compound is obtained as oil.

Workup

  1. stirringthe mixture is stirred for 18 hours at room temperature
  2. concentrationAfter the concentration
  3. customby evaporation, it
  4. additionis mixed with water
  5. extractionextracted with ethyl acetate
  6. extractionThe extract that
  7. concentrationhas been concentrated by evaporation
  8. additionis mixed with diethyl ether
  9. filtrationfiltered
  10. customThe filtrate is purified by column chromatography

Sources & evidence

ORD record
ord-74f2adb3536b4ffe895d28a078809237
Source dataset
uspto-grants-1993_10
Patent number
US05256682

Reaction notes

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