2-Aminobenzenesulfonamide → Ethyl 3-[2-(aminosulfonyl)anilino]-3-oxopropanoate

HRID 884248Notes

Reaction equation

HRID 884248 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].[CH2:12]([O:14][C:15](=[O:20])[CH2:16][C:17](Cl)=[O:18])[CH3:13]>CN(C)C(=O)C.C(OCC)C>[CH2:12]([O:14][C:15](=[O:20])[CH2:16][C:17]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](=[O:9])(=[O:10])[NH2:11])=[O:18])[CH3:13]

Participants

5

Reactant 2

HCID 728942-AminobenzenesulfonamideHCID 118931Ethyl 3-chloro-3-oxopropionate

Product 1

HCID 14674447Ethyl 3-[2-(aminosulfonyl)anilino]-3-oxopropanoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
25 °C

Procedure

2-Amino-benzenesulfonamide (5 g, 29 mmol) was dissolved in N,N-dimethylacetamide (25 mL) and diethyl ether (25 mL). Ethyl-3-chloro-3-oxo-propionate (4.6 g, 30.45 mmol) was added into the above reaction solution. The reaction mixture was stirred at 25° C. for 3 h. The product started to precipitate and was collected by vacuum filtration. The solid was dissolved in ethyl acetate (200 mL) and extracted with water (200 mL). The aqueous layer was back-extracted with ethyl acetate (200 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to afford the crude product, N-(2-sulfamoyl-phenyl)-malonamic acid ethyl ester, as a white solid, which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ: 1.23 (3H, t, J=7.0 Hz), 3.61 (2H, s), 4.14 (2H, quartet, J=7.0 Hz), 7.29-7.33 (1H, m), 7.53 (2H, bs), 7.56-7.60 (1H, m), 7.84-7.86 (1H, m), 7.97-7.99 (1H, m), 9.54 (1H, bs). LC-MS (ESI) calcd for C11H14N2O5S 286.06, found 287.1 [M+H+].

Workup

  1. customto precipitate
  2. filtrationwas collected by vacuum filtration
  3. dissolutionThe solid was dissolved in ethyl acetate (200 mL)
  4. extractionextracted with water (200 mL)
  5. extractionThe aqueous layer was back-extracted with ethyl acetate (200 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-272396264f3249a88fcbfa96aa42b373
Source dataset
uspto-grants-2012_08
Patent number
US08236948B2

Reaction notes

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