Water → HCID 67557502, compound

HRID 342465Notes

Reaction equation

HRID 342465 reaction equation
Cl[CH2:2][C:3]1[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14](=[O:23])[C:15]3[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:22])[C:5]=2[O:6][C:7]=1[CH3:8].[C:24](=O)([O-])[O-:25].[K+].[K+].O>CO>[Cl:21][C:20]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:22])[C:15]=1[C:14]([NH:13][C:9]1[C:5]2[O:6][C:7]([O:25][CH3:24])([CH3:8])[C:3](=[CH2:2])[C:4]=2[CH:12]=[CH:11][CH:10]=1)=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 70200093HCID 70200093, compound

Product 1

HCID 67557502HCID 67557502, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-chloromethyl-7-(2,6-dichlorobenzoylamino)-2-methylbenzo[b]furan (20 mg) and potassium carbonate (7.5 mg) in methanol was refluxed for 1 hour. The mixture was cooled and poured into water. The separated oil was extracted with ethyl acetate and the extract was washed with water, dried over sodium sulfate and evaporated in vacuo. The residue was purified by preparative TLC to give 7-(2,6-dichlorobenzoylamino)-2,3-dihydro-2-methoxy-2-methyl-3-methylenebenzo[b]furan (5 mg).

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureThe mixture was cooled
  3. extractionThe separated oil was extracted with ethyl acetate
  4. washthe extract was washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-600058821b8148ffb1caf700fb7b67d5
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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