Hydrochloric Acid → HCID 18347079, compound

HRID 2269422Notes

Reaction equation

HRID 2269422 reaction equation
CO[C:3]1[C:4](=[O:10])[C:5](=[O:9])[C:6]=1[O:7][CH3:8].Cl.[NH2:12][C:13]1[CH:14]=[C:15]([CH:19]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[NH:20][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]=[CH:17][CH:18]=1.C(N(CC)CC)C.Cl>CO>[CH3:8][O:7][C:6]1[C:5](=[O:9])[C:4](=[O:10])[C:3]=1[NH:12][C:13]1[CH:14]=[C:15]([CH:19]([C:29]2[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)[NH:20][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 1232273-Cyclobutene-1,2-dione, 3,4-dimethoxy-HCID 18334159HCID 18334159, compound

Product 1

HCID 18347079HCID 18347079, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3,4-dimethoxy-3-cyclobutene-1,2-dione (428 mg) was added to a solution of N-[(3-aminophenyl)-(4-methoxyphenyl)methyl]benzamide hydrochloride (555 mg) [prepared as described in step (d) above] in methanol (15 ml) at ambient temperature. After stirring for 10 minutes, a solution of triethylamine (153 mg) in methanol (10 ml) was added dropwise to the mixture. This mixture was stirred at ambient temperature for 1 hour. The reaction mixture was then slightly acidified with hydrochloric acid (0.5N) and extracted with ethyl acetate. The organic extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by chromatography through a silica gel column using a 1:1 by volume mixture of hexane and ethyl acetate as the eluant, to afford the title compound (505 mg) as a white foamy solid.

Workup

  1. stirringThis mixture was stirred at ambient temperature for 1 hour
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe residue was purified by chromatography through a silica gel column
  8. additionby volume mixture of hexane and ethyl acetate as the eluant

Sources & evidence

ORD record
ord-3924d4e6aeee447883000996b3529d6e
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

Loading…