Hydrochloric Acid → HCID 178488948, compound

HRID 235958Notes

Reaction equation

HRID 235958 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[CH:5][CH:4]=1.[ClH:15]>O>[Cl:15][C:11]1[NH:10][C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[N:13][C:12]=1[CH3:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178488953HCID 178488953, compound

Product 1

HCID 178488948HCID 178488948, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A suspension of 2-(p-methoxyphenyl)-4-methylimidazole, (4.5 g, 0.024 mole) in concentrated HCl (96 ml)--H2O (34 ml) was stirred vigorously while a solution of KClO3 (1 g) in H2O (50 ml) was added dropwise over 11/4 hour. The precipitated hydrochloride salt was collected and suspended in H2O (200 ml), saturated Na2CO3 solution (50 ml). After an overnight period of stirring, the solid was collected, chromatographed on silica gel, the product eluted with 5% CH3OH--CHCl3 and crystallized from 50% CH3CN to yield 0.9 g (17%) of 38, m.p. 182°-186° C. A sample recrystallized from 50% CH3CN melted at 185°-187° C.

Workup

  1. additionwas added dropwise over 11/4 hour
  2. customThe precipitated hydrochloride salt was collected
  3. customthe solid was collected
  4. customchromatographed on silica gel
  5. washthe product eluted with 5% CH3OH
  6. customCHCl3 and crystallized from 50% CH3CN

Sources & evidence

ORD record
ord-038092e68c214dfab3195bdfbd05d61e
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

Loading…