Sodium Bicarbonate → HCID 18612735, compound

HRID 1180558Notes

Reaction equation

HRID 1180558 reaction equation
[C:1]([NH:4][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:3])[CH3:2].C(=O)(O)[O-].[Na+]>CO>[C:1]([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:17])=[O:16])[CH:9]([C:10]([O:12][CH3:13])=[O:11])[CH2:14]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 516892Sodium Bicarbonate2×HCID 18613053HCID 18613053, compound

Product 1

HCID 18612735HCID 18612735, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-[(2-acetylamino-benzyl)-(4-methoxybenzenesulfonyl)amino]acrylate (8.40 g, 20.07 mmol) in anhydrous methanol (5 ml) was added anhydrous sodium bicarbonate (2.19 g, 26.09 mmol) and the mixture was stirred at room temperature overnight. Anhydrous sodium bicarbonate (2.2 g) was added and the mixture was stirred for 18 hours, heated to 50° C. for three hours and the solvent removed in vacuo. The residue was dissolved in water and ethyl acetate. The organic layer was separated, washed with saturated sodium chloride and dried with anhydrous sodium sulfate. The solvent was removed in vacuo and the residue dried in vacuo to give 6.64 g of white crystals, m.p. 150-155° C.

Workup

  1. stirringthe mixture was stirred for 18 hours
  2. temperatureheated to 50° C. for three hours
  3. customthe solvent removed in vacuo
  4. dissolutionThe residue was dissolved in water
  5. customThe organic layer was separated
  6. washwashed with saturated sodium chloride
  7. dry with materialdried with anhydrous sodium sulfate
  8. customThe solvent was removed in vacuo
  9. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-21acd2bac17f42238b98403f49c5fd1b
Source dataset
uspto-grants-2007_10
Patent number
US07282496B2

Reaction notes

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