Sodium Carbonate → HCID 23568419, compound

HRID 1822724Notes

Reaction equation

HRID 1822724 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([N:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])#[N:2].Cl.[CH3:16][NH:17][OH:18].C(=O)([O-])[O-].[Na+].[Na+].[C:25]([C:32]([O:34][CH2:35][CH3:36])=[O:33])#[C:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(O)C.O.C(O)C>[CH2:35]([O:34][C:32]([C:25]1([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[O:18][N:17]([CH3:16])[C:1]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[S:9](=[O:11])(=[O:10])[N:12]([CH3:14])[CH3:13])=[N:2]1)=[O:33])[CH3:36]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 69803Diethyl acetylenedicarboxylateHCID 77906N-methylhydroxylamine hydrochlorideHCID 6978732-cyano-N,N-dimethylbenzenesulfonamide

Product 1

HCID 23568419HCID 23568419, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-cyano-N,N-dimethyl-benzenesulfonamide (4.68 g, 22.3 mmol) in ethanol/water (1:1, 150 mL) was added N-methylhydroxylamine hydrochloride (3.72 g, 44.6 mmol) followed by sodium carbonate (2.36 g, 22.3 mmol). The resulting mixture was stirred at 90° C. for 8 h then concentrated. The residue was triturated with MeOH/CHCl3 (10%) and filtered. The solution was concentrated leaving an orange residue that was dissolved in ethanol (50 mL). Added to this solution was diethyl acetylene-dicarboxylate (3.6 mL, 22.3 mmol) and the resulting mixture stirred at room temp for 30 min. The mixture was concentrated and purified by flash chromatography (25% to 50% EtOAc/Hexanes) to give the title product as a yellow oil (5.57 g, 58% over two steps). 1HNMR (300 MHz, CDCl3) δ: 7.93–7.87 (1H, m), 7.66–7.60 (2H, m), 7.57–7.51 (1H, m), 4.39–4.22 (2H,m), 4.16 (q, 2H, J=7.20 Hz), 3.40 (1H, d, J=16.47 Hz), 3.15 (1H, d, J=16.47 Hz), 3.00 (3H, s), 2.82 (6H, s), 1.24 (6H, td, J=6.95, 1.46 Hz). LCMS calcd for C18H26N3O7S (M+H): 428.14; found: 428.10.

Workup

  1. concentrationthen concentrated
  2. customThe residue was triturated with MeOH/CHCl3 (10%)
  3. filtrationfiltered
  4. concentrationThe solution was concentrated
  5. customleaving an orange residue that
  6. additionAdded to this solution
  7. stirringthe resulting mixture stirred at room temp for 30 min
  8. concentrationThe mixture was concentrated
  9. custompurified by flash chromatography (25% to 50% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-e0b1c877153e4994bfb67eadf5c22e7c
Source dataset
uspto-grants-2006_05
Patent number
US07037908B2

Reaction notes

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