Water → HCID 14211364, compound

HRID 620830Notes

Reaction equation

HRID 620830 reaction equation
C([NH:4][C:5]1[C:10]([Cl:11])=[CH:9][C:8]([C:12]2[NH:13][C:14]([CH3:23])=[C:15]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[N:16]=2)=[C:7]([O:24][CH3:25])[CH:6]=1)(=O)C.O>Cl>[NH2:4][C:5]1[C:10]([Cl:11])=[CH:9][C:8]([C:12]2[NH:13][C:14]([CH3:23])=[C:15]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[N:16]=2)=[C:7]([O:24][CH3:25])[CH:6]=1

Participants

4

Reactant 2

HCID 962WaterHCID 9998411HCID 9998411, compound

Product 1

HCID 14211364HCID 14211364, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-(4-acetamido-5-chloro-2-methoxyphenyl)-5-methyl-4-(3-pyridyl)imidazole (1.0 g) in 10% hydrochloric acid (30 ml) was stirred at 80° to 85° C. for 4 hours. The reaction mixture was poured into water (100 ml) and washed with ethyl acetate. The solution was adjusted to pH 8.0 with 20% potassium carbonate and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was crystallized from a mixture of ethyl acetate and diethyl ether to give 2-(4-amino-5-chloro-2-methoxyphenyl)-5-methyl-4-(3-pyridyl)imidazole (0.63 g).

Workup

  1. washwashed with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was crystallized from a mixture of ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-1d11e45cd5ec4f4aa32b8af6773877b8
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

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