Sodium Bicarbonate → HCID 18612735, compound

HRID 1420596Notes

Reaction equation

HRID 1420596 reaction equation
C([N:4]([C:30](=[O:32])[CH3:31])[C:5]1[CH:29]=[CH:28][CH:27]=[CH:26][C:6]=1[CH2:7][N:8]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[C:9](=[CH2:14])[C:10]([O:12][CH3:13])=[O:11])(=O)C.C(=O)(O)[O-].[Na+]>CO>[C:30]([N:4]1[C:5]2[CH:29]=[CH:28][CH:27]=[CH:26][C:6]=2[CH2:7][N:8]([S:15]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)(=[O:16])=[O:17])[CH:9]([C:10]([O:12][CH3:13])=[O:11])[CH2:14]1)(=[O:32])[CH3:31]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 18612823Methyl 2-[(2-diacetylaminobenzyl)-(4-methoxybenzenesulfonyl)amino]acrylate

Product 1

HCID 18612735HCID 18612735, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.70 g (1.52 mmol) of methyl 2-[(2-diacetylaminobenzyl)-(4-methoxybenzenesulfonyl)amino]acrylate in 5 ml of anhydrous methanol was added 0.332 g (3.95 mmol) of anhydrous sodium bicarbonate. The mixture was stirred at room temperature overnight and the solvent removed under vacuum. To the residue was added ethyl acetate and H2O. The organic layer was separated, washed with brine and dried with Na2SO4. The solvent was removed and the residue dried under vacuum to give 0.59 g of white crystals, m.p. 150-155° C. Anal. for C20H22N2O6S: Calc'd: C,57.4; H,5.3; N,6.7; S,7.7; Found: C,56.6; H,5.2; N,6.5; S,7.5; Mass spectrum (ES) 419.9 (M+H).

Workup

  1. customthe solvent removed under vacuum
  2. additionTo the residue was added ethyl acetate and H2O
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried with Na2SO4
  6. customThe solvent was removed
  7. customthe residue dried under vacuum

Sources & evidence

ORD record
ord-67b772de02604e81a1bef3fd27f29ba5
Source dataset
uspto-grants-2000_06
Patent number
US06071903

Reaction notes

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