Iodoethane → HCID 66720186, compound

HRID 348519Notes

Reaction equation

HRID 348519 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=3)=[O:5])[CH3:2].[H-].[Na+].[CH2:23](I)[CH3:24]>CN(C=O)C.[NH4+].[Cl-].O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH2:23][CH3:24])[C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 66720295Ethyl 6-methoxy-9H-carbazole-3-carboxylate

Product 1

HCID 66720186HCID 66720186, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

A solution of 6-methoxycarbazole-3-carboxylic acid ethyl ester (1.28 g, 4.77 mmol) in DMF (8 mL) was added to a suspension of sodium hydride (60% in mineral oil, 0.286 mg, 7.15 mmol) in DMF at 0° C. The reaction was stirred for 30 minutes then ethyl iodide was added (0.89 g, 5.72 mmol). The reaction was allowed to reach room temperature and was stirred for further 15 hours then was diluted with NH4Cl sat. and water. The reaction was extracted with tert-butylmethyl ether and the organic phase was washed with water then brine. The organic layer was dried over sodium sulfate and the solvent concentrated in vacuo to give a crude which was purified by column (10% ethyl acetate/hexane) to afford 0.79 g of the title compound.

Workup

  1. customto reach room temperature
  2. stirringwas stirred for further 15 hours
  3. extractionThe reaction was extracted with tert-butylmethyl ether
  4. washthe organic phase was washed with water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationthe solvent concentrated in vacuo
  7. customto give a crude which
  8. customwas purified by column (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-527c9943c4d04d53b07c1f3a6cb9adcc
Source dataset
uspto-grants-2007_02
Patent number
US07176322B2

Reaction notes

Loading…