N-(2-(6-Chloro-5-methoxy-1H-indol-3-yl)ethyl)acetamide → HCID 21263053, compound

HRID 371684Notes

Reaction equation

HRID 371684 reaction equation
CN(C)C=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][C:16]=1[Cl:17])[NH:13][CH:12]=[C:11]2[CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22].[H-].[Na+].[C:26](Cl)(=[O:28])[CH3:27]>C(O)(=O)C>[C:26]([N:13]1[C:14]2[C:10](=[CH:9][C:8]([O:7][CH3:6])=[C:16]([Cl:17])[CH:15]=2)[C:11]([CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22])=[CH:12]1)(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 1858N-(2-(6-Chloro-5-methoxy-1H-indol-3-yl)ethyl)acetamideHCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 24758Sodium hydride

Product 1

HCID 21263053HCID 21263053, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 30 ml. of N,N-dimethylformamide were added 210.7 mg. (0.79 mmole) of N-[2-(5-methoxy-6-chloroindol-3-yl)ethyl]acetamide (prepared as in Example 1) followed by 20.8 mg. of sodium hydride. The resulting mixture was stirred at room temperature for about one hour, and 68.2 mg. (0.06 ml.) of acetyl chloride were added. The mixture was stirred for an additional hour and then was poured into ice water containing a small amount of acetic acid. The resulting mixture was extracted with chloroform, and the extract was washed twice with saturation aqueous sodium chloride solution. The chloroform extract was dried over sodium sulfate and was concentrated in a rotary evaporator. The residue was recrystallized from benzene-ether and was vacuum-dried to obtain 108 mg. (40.8%) of the title compound, m.p. 178°-181° C.

Workup

  1. stirringThe mixture was stirred for an additional hour
  2. extractionThe resulting mixture was extracted with chloroform
  3. washthe extract was washed twice with saturation aqueous sodium chloride solution
  4. extractionThe chloroform extract
  5. dry with materialwas dried over sodium sulfate
  6. concentrationwas concentrated in a rotary evaporator
  7. customThe residue was recrystallized from benzene-ether
  8. customwas vacuum-dried
  9. customto obtain 108 mg

Sources & evidence

ORD record
ord-027463e207234d22b686ec7ba23201f3
Source dataset
uspto-grants-1978_05
Patent number
US04087444

Reaction notes

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