1-Methylimidazole → HCID 21087646, compound

HRID 1264440Notes

Reaction equation

HRID 1264440 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.[Cl:7][CH2:8][C:9]([NH:11][C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([CH3:19])=[C:14]([Cl:20])[C:13]=1[OH:21])=[O:10]>C(OCC)(=O)C>[Cl-:7].[Cl:20][C:14]1[C:13]([OH:21])=[C:12]([NH:11][C:9]([CH2:8][N:4]2[CH:5]=[CH:6][N+:2]([CH3:1])=[CH:3]2)=[O:10])[CH:17]=[C:16]([Cl:18])[C:15]=1[CH3:19]

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 18552008HCID 18552008, compound

Product 1

HCID 21087646HCID 21087646, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4.45 ml of N-methylimidazole (56 mmol) were added to a suspension of 5 g of 2-chloro-N-(3,5-dichloro-2-hydroxy-4-methylphenyl)acetamide (18.6 mmol), obtained above in the preceding step, in 5 ml of ethyl acetate, leading to a clear solution. After 3 hours and 30 minutes, the insoluble product which formed was drained and abundantly washed with ethyl acetate. The new precipitate which formed in the filtrates was drained and abundantly washed with ethyl acetate. The white powders thus obtained were combined and dried to give 5 g of 3-[(3,5-dichloro-2-hydroxy-4-methylphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride whose melting point was 251° C., (yield 77%).

Workup

  1. custom30 minutes, the insoluble product which formed
  2. washabundantly washed with ethyl acetate
  3. customThe new precipitate which formed in the filtrates
  4. washabundantly washed with ethyl acetate
  5. customThe white powders thus obtained
  6. customdried

Sources & evidence

ORD record
ord-f54909df51a541dfa492794f9027dac6
Source dataset
uspto-grants-2003_04
Patent number
US06544298B1

Reaction notes

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