Hydrochloric Acid → HCID 178488948, compound

HRID 1722008Notes

Reaction equation

HRID 1722008 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 KC103 (1 g) in H2O (50 ml) was added dropwise over 1-1/4 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 1-1/4 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-CHCl3
  6. customcrystallized from 50% CH3CN

Sources & evidence

ORD record
ord-535180fd7d1e49519821eff26c485471
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

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