Hydrochloric Acid → HCID 15523743, compound

HRID 323711Notes

Reaction equation

HRID 323711 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]2([Cl:16])[Cl:15])(=[O:4])=[O:3].[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>C(Cl)Cl>[CH2:17]([NH:24][S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]2([Cl:16])[Cl:15])(=[O:4])=[O:3])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 30223523,3-Dichloro-2-oxoindoline-5-sulphonyl chloride

Product 1

HCID 15523743HCID 15523743, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-chlorosulfonyl-3,3-dichloro-2-oxindole (100 mg, 400 umol) in methylene chloride (3 mL) was added benzylamine (135 uL, 1.2 mmol) dropwise. After stirring for 4 h. 3 N hydrochloric acid was added along with an additional volume of methylene chloride (20 mL). The organic layer was dried over magnesium sulfate, filtered, and silica gel flash chromatography (25 to 35% ethyl acetate/hexanes) yielded the title compound. ES (−) MS m/e=369 (M−H).

Workup

  1. dry with materialThe organic layer was dried over magnesium sulfate
  2. filtrationfiltered

Sources & evidence

ORD record
ord-28fd0c34a1de4e32a7eab91ae88204ea
Source dataset
uspto-grants-2001_04
Patent number
US06214858B1

Reaction notes

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