Hydrochloric Acid → HCID 69946028, compound

HRID 323712Notes

Reaction equation

HRID 323712 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:14])[C:9](=[O:15])[C:8]2([Cl:17])[Cl:16])(=[O:4])=[O:3].[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>C(Cl)Cl>[CH2:18]([NH:25][S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:14])[C:9](=[O:15])[C:8]2([Cl:17])[Cl:16])(=[O:4])=[O:3])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 86756607HCID 86756607, compound

Product 1

HCID 69946028HCID 69946028, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-chlorosulfonyl-N-methyl-3,3-dichloro-2-oxindole (120 mg, 382 umol) in methylene chloride (5 mL) was added benzyl amine (50 uL, 458 umol) dropwise. After stirring overnight, 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 (35 to 55% ethyl acetate/hexanes) yielded the title compound. ES (−) MS m/e=383 (M−H).

Workup

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

Sources & evidence

ORD record
ord-c08ec77a261a459fafad73c64cab26e7
Source dataset
uspto-grants-2001_04
Patent number
US06214858B1

Reaction notes

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