1-Methylimidazole → HCID 21087650, compound

HRID 395226Notes

Reaction equation

HRID 395226 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.[C:7]([NH:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][C:15]([NH:22][C:23](=[O:26])[CH2:24][Cl:25])=[C:16]2[OH:21])(=[O:9])[CH3:8]>O1CCOCC1>[Cl-:25].[OH:21][C:16]1[C:17]2[C:12](=[C:11]([NH:10][C:7](=[O:9])[CH3:8])[CH:20]=[CH:19][CH:18]=2)[CH:13]=[CH:14][C:15]=1[NH:22][C:23]([CH2:24][N:4]1[CH:5]=[CH:6][N+:2]([CH3:1])=[CH:3]1)=[O:26]

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 18172725HCID 18172725, compound

Product 1

HCID 21087650HCID 21087650, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.25 ml of N-methylimidazole (3.1 mmol) was introduced into a solution of N-(5-acetylamino-1-hydroxynaphthalen-2-yl)-2-chloroacetamide obtained above in step d) (0.9 g, 3 mmol) in 20 ml of dioxane. The reaction medium was heated under reflux for 7 hours and 30 minutes. The precipitate formed was drained, washed abundantly with dioxane and dried under vacuum to constant weight to give 0.82 g of 3-[(1-hydroxy-5-acetylaminonaphthalen-2-ylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride in the form of a red powder melting at 168° C. and with a yield of 73%. Cation mass spectroscopy analysis: m/z=338 of the product obtained was consistent with that of the product obtained.

Workup

  1. temperatureThe reaction medium was heated
  2. temperatureunder reflux for 7 hours and 30 minutes
  3. customThe precipitate formed
  4. washwashed abundantly with dioxane
  5. customdried under vacuum to constant weight

Sources & evidence

ORD record
ord-f668073e1b7c465782f7cd9321fae41a
Source dataset
uspto-grants-2003_08
Patent number
US06605124B1

Reaction notes

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