Hydrochloric Acid → HCID 18369261, compound

HRID 1699732Notes

Reaction equation

HRID 1699732 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([S:11]([NH2:14])(=[O:13])=[O:12])=[C:4]([Cl:15])[CH:3]=1.Cl.C(O)C.O=[C:21]([C:27](OCC)=[O:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>CO.[C].[Pd]>[NH2:14][S:11]([C:5]1[CH:6]=[C:7]2[C:2](=[CH:3][C:4]=1[Cl:15])[N:1]=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:27](=[O:28])[NH:8]2)(=[O:13])=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 691051,3-Diethyl 2-oxopropanedioateHCID 13289687HCID 13289687, compound

Product 1

HCID 18369261HCID 18369261, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-amino-2-chloro-5-nitrobenzenesulfonamide (2.00 g, 7.95 mmol) in methanol (40 ml) were added 10% palladium-carbon (400 mg) and successively 10% hydrochloric acid (6 ml) at room temperature, and catalytic hydrogenation was conducted for 2 hours at ambient temperature under ambient pressure. Catalyst was filtered off using celite and the filtrate was distilled off under reduced pressure. After dissolved this into ethanol (16 ml), diethyl ketomalonate (1.21 ml, 7.95 mmol) was added, which was stirred for 5 hours at room temperature. The precipitate was collected by filtration, washed with ethanol and then purified by means of silica gel column chromatography [hexane-ethyl acetate=1:2] to obtain 288 mg of the title compound. Yield 11%.

Workup

  1. filtrationCatalyst was filtered off
  2. distillationthe filtrate was distilled off under reduced pressure
  3. additionwas added
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with ethanol
  6. custompurified by means of silica gel column chromatography [hexane-ethyl acetate=1:2]

Sources & evidence

ORD record
ord-09410ca8ebc14a2f80c6d5e21e3bcfe2
Source dataset
uspto-grants-2002_02
Patent number
US06348461B1

Reaction notes

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