Ammonium Chloride → HCID 11473887, compound

HRID 430743Notes

Reaction equation

HRID 430743 reaction equation
[C:1]1([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[SH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].Cl[CH2:22][C:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[C:31]([O:32][CH3:33])[C:26]=2[O:25][CH:24]=1.[Cl-].[NH4+]>CN(C=O)C>[C:9]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[S:8][CH2:22][C:23]2[C:27]3[CH:28]=[CH:29][CH:30]=[C:31]([O:32][CH3:33])[C:26]=3[O:25][CH:24]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 138160DiphenylmethanethiolHCID 18351661HCID 18351661, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 11473887HCID 11473887, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon atmosphere, diphenylmethanethiol (121 mg) was dissolved in DMF (2 ml) and the solution was stirred at room temperature. To this solution, potassium t-butoxide (81 mg) and 3-chloromethyl-7-methoxybenzofuran (118 mg) were added and the solution was stirred at room temperature. After confirming vanishment of the materials, the reaction solution was poured into saturated aqueous ammonium chloride solution (5 ml) and the resulting solution was extracted three times with ethyl acetate (10 ml). The organic layers were combined and washed with saturated brine, followed by drying the resultant over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=20/1) using silica gel to obtain the desired compound (183 mg, yield: 85%).

Workup

  1. stirringthe solution was stirred at room temperature
  2. extractionthe resulting solution was extracted three times with ethyl acetate (10 ml)
  3. washwashed with saturated brine
  4. dry with materialby drying the resultant over sodium sulfate
  5. customAfter removing the sodium sulfate
  6. filtrationby filtration
  7. customthe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-524298e2390d44b689341033d07e05d1
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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