1-Methylimidazole → HCID 21087648, compound

HRID 1264441Notes

Reaction equation

HRID 1264441 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.[C:7]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:21])[CH2:19][Cl:20])=[C:13]([OH:22])[CH:12]=1)(=[O:9])[CH3:8]>C(OCC)(=O)C.O>[Cl-:20].[C:7]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([CH2:19][N:4]2[CH:5]=[CH:6][N+:2]([CH3:1])=[CH:3]2)=[O:21])=[C:13]([OH:22])[CH:12]=1)(=[O:9])[CH3:8]

Participants

5

Reactant 2

HCID 13901-MethylimidazoleHCID 18552100HCID 18552100, compound

Product 1

HCID 21087648HCID 21087648, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

9.85 ml of N-methylimidazole (123 mmol) were added to a suspension of 10 g (41 mmol) of N-(4-acetylamino-2-hydroxyphenyl)-2-chloroacetamide obtained above in the preceding step in 30 ml of ethyl acetate. The reaction medium was heated under reflux for 6 hours and then the insoluble product formed was drained and abundantly washed with ethyl acetate. The brown solid thus obtained was taken up in water and filtered and then the filtrate was poured over dioxane. The precipitate obtained was drained, abundantly washed with dioxane and then with isopropyl ether and dried under vacuum to give 10.6 g of 3-[(4-acetylamino-2-hydroxyphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride in the form of a purple-brown powder whose melting point was 225° C., (yield 79%).

Workup

  1. temperatureThe reaction medium was heated
  2. temperatureunder reflux for 6 hours
  3. customthe insoluble product formed
  4. washabundantly washed with ethyl acetate
  5. customThe brown solid thus obtained
  6. filtrationfiltered
  7. additionthe filtrate was poured over dioxane
  8. customThe precipitate obtained
  9. washabundantly washed with dioxane
  10. dry with materialwith isopropyl ether and dried under vacuum

Sources & evidence

ORD record
ord-f822467e02804c5ab814a6e71ce8bcdd
Source dataset
uspto-grants-2003_04
Patent number
US06544298B1

Reaction notes

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