Bis-(1H-imidazol-2-YL)-methanone → HCID 14687318, compound

HRID 2052562Notes

Reaction equation

HRID 2052562 reaction equation
[NH2:1][CH:2]([CH3:15])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1)[OH:4].[C:16](C1NC=CN=1)(C1NC=CN=1)=[O:17]>C(Cl)(Cl)Cl>[CH3:14][O:13][C:7]1[CH:6]=[C:5]([CH:3]2[O:4][C:16](=[O:17])[NH:1][CH:2]2[CH3:15])[CH:10]=[CH:9][C:8]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 13585934HCID 13585934, compound

Product 1

HCID 14687318HCID 14687318, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5.5 mmol of 2-amino-(3,4-dimethoxyphenyl)-propanol is dissolved in 50 ml. of chloroform and stirred with 1.05 g. (6.5 mmol) of carbonyl diimidazole for 2 hours under the exclusion of moisture. After allowing the reaction mixture to stand overnight, the mixture is extracted with the use of 50 ml. of distilled water, dried, filtered, and concentrated. After chromatography of the residue over 50 g. of silica gel with chloroform/methanol (95:5) as the eluent and recrystallization from ethyl acetate/petroleum ether, a 24% yield is obtained of 5-(3,4-dimethoxyphenyl)-4-methyl-2-oxazolidinone, m.p. 98°-99°.

Workup

  1. extractionthe mixture is extracted with the use of 50 ml
  2. dry with materialof distilled water, dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customof silica gel with chloroform/methanol (95:5) as the eluent and recrystallization from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-81f8416ec4dd45dc934df7ef2699217f
Source dataset
uspto-grants-1980_01
Patent number
US04186129

Reaction notes

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