Hydrochloric Acid → HCID 22228573, compound

HRID 1173104Notes

Reaction equation

HRID 1173104 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:8]=[C:9]([S:13]([NH:16][C:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[C:25]=2[NH:24][CH:23]=[CH:22]3)(=[O:15])=[O:14])[CH:10]=[CH:11][CH:12]=1.[OH-].[Na+].Cl.CN(C)[CH:31]=[O:32]>O>[Cl:6][C:7]1[CH:8]=[C:9]([S:13]([NH:16][C:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[C:25]=2[NH:24][CH:23]=[C:22]3[CH:31]=[O:32])(=[O:14])=[O:15])[CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 19080180HCID 19080180, compound

Product 1

HCID 22228573HCID 22228573, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.3 ml (13.9 mmol) of phosphorous oxychloride was added dropwise to 14.5 ml of dimethylformamide at 10° C. or less under stirring in nitrogen atmosphere. After stirring at about 5° C. for 30 minutes, 2.50 g (8.15 mmol) of 3-chloro-N-(1H-indole-7-yl)benzenesulfonamide synthesized in the same manner as in Example 1 was added thereto in three portions. After stirring at about 5° C. for further 30 minutes, 200 ml of cooled water was added thereto. The reaction mixture was adjusted to pH about 14 by adding a 1N aqueous sodium hydroxide and then to pH about 2 by adding 1N hydrochloric acid, and then extracted by adding ethyl acetate thereto. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography, to give 1.45 g of the title compound.

Workup

  1. stirringAfter stirring at about 5° C. for 30 minutes
  2. additionwas added
  3. stirringAfter stirring at about 5° C. for further 30 minutes
  4. extractionextracted
  5. additionby adding ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-61b8be5138a8475eaccadf52e80ab50a
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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