Sodium Carbonate → HCID 178472137, compound

HRID 1168529Notes

Reaction equation

HRID 1168529 reaction equation
[CH:1]([N:3]([CH3:5])[NH2:4])=[O:2].[F:6][C:7]1[C:24]([F:25])=[CH:23][C:22]([I:26])=[CH:21][C:8]=1[C:9]([C:11](=[CH:17]OCC)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[F:6][C:7]1[C:24]([F:25])=[CH:23][C:22]([I:26])=[CH:21][C:8]=1[C:9]([C:11](=[CH:17][NH:4][N:3]([CH:1]=[O:2])[CH3:5])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 12962Hydrazinecarboxaldehyde, 1-methyl-HCID 69879816Ethyl 2-(2,3-Difluoro-5-iodobenzoyl)-3-ethoxy-2-propenoate

Product 1

HCID 178472137HCID 178472137, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A solution of 1-formyl-1-methylhydrazine (0.217 g) in toluene (0.5 mL) is added to a solution of ethyl 2-(2,3-difluoro-5-iodobenzoyl)-3-ethoxy-2-propenoate (Preparation 21, 1.00 g) in toluene (2.5 mL) at 33° C. After stirring at ambient temperature for 20 minutes, a precipitate formed and an additional 1.5 mL of toluene is added. After an additional 1.75 h, solid anhydrous Na2CO3 (0.285 g) is added and the reaction mixture is heated to reflux. After 1 h, the reaction mixture is concentrated at reduced pressure and the residue suspended in 8 mL of water which is used as is in the following step. Physical characteristics: MS (ESI+) m/z 419 (M+H)+.

Workup

  1. customa precipitate formed
  2. waitAfter an additional 1.75 h
  3. temperaturethe reaction mixture is heated to reflux
  4. waitAfter 1 h
  5. concentrationthe reaction mixture is concentrated at reduced pressure

Sources & evidence

ORD record
ord-9e8961366057427c8c487a5a6fc100ca
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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