Dimethylformamide → HCID 18976105, compound

HRID 2393508Notes

Reaction equation

HRID 2393508 reaction equation
S(Cl)([Cl:3])=O.CN(C=O)C.[C:10]1([S:16]([N:19]2[C:31]3[CH:30]=[C:29]([CH:32](O)[CH3:33])[CH:28]=[CH:27][C:26]=3[C:25]3[C:20]2=[CH:21][CH:22]=[CH:23][CH:24]=3)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl>[C:10]1([S:16]([N:19]2[C:31]3[CH:30]=[C:29]([CH:32]([Cl:3])[CH3:33])[CH:28]=[CH:27][C:26]=3[C:25]3[C:20]2=[CH:21][CH:22]=[CH:23][CH:24]=3)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 18976101HCID 18976101, compound

Product 1

HCID 18976105HCID 18976105, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.26 ml, 3.54 mmol) and catalytically effective amount of DMF were added at room temperature to a solution of 9-benzenesulfonyl-2-(1-hydroxyethyl)carbazole (0.621 g, 1.77 mmol) in methylene chloride, and the mixture was heated under reflux for 1.5 hours. After evaporation of the solvent under reduced pressure, the thus obtained residue was mixed with ethyl acetate and washed with saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution in that order, the organic layer was dried over magnesium sulfate and then the solvent was evaporated under reduced pressure to obtain 9-benzenesulfonyl-2-(1-chloroethyl)carbazole.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. customAfter evaporation of the solvent under reduced pressure
  4. additionthe thus obtained residue was mixed with ethyl acetate
  5. washwashed with saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution in that order
  6. dry with materialthe organic layer was dried over magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4364d56930964951a11ff56bdc085e52
Source dataset
uspto-grants-1998_09
Patent number
US05807880

Reaction notes

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