Sodium Bicarbonate → HCID 178515368, compound

HRID 1926254Notes

Reaction equation

HRID 1926254 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[CH2:4][NH:5][C:6](=[O:12])[CH:7](OC)OC.C([O-])(O)=O.[Na+]>S(=O)(=O)(O)O>[Cl:17][C:14]1[CH:15]=[CH:16][C:2]([Cl:1])=[C:3]2[C:13]=1[CH:7]=[C:6]([OH:12])[N:5]=[CH:4]2

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67520605N-(2,5-dichlorobenzyl)-2,2-dimethoxyacetamide

Product 1

HCID 178515368HCID 178515368, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of N-(2,5-dichlorobenzyl)-2,2-dimethoxyacetamide (1.0 g, 3.6 mmol) in sulfuric acid (18M; 4 mL) was stirred at 50° C. for 1 h. The reaction mixture was charged with ice and neutralized with NaHCO3. The aqueous mixture was extracted with 5% MeOH in DCM (3×), washed with NaHCO3, dried over sodium sulfate, filtered and concentrated to afford the title compound as yellow solid. MS (ES+): m/z=215.75/217.75 (3:1) [MH+]. HPLC: tR=2.76 min (ZQ2, polar—5 min).

Workup

  1. extractionThe aqueous mixture was extracted with 5% MeOH in DCM (3×)
  2. washwashed with NaHCO3
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5be2e78bb4fd44f6a9b795960d4cd99f
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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