Methyl iodide → HCID 4249922, compound

HRID 1379798Notes

Reaction equation

HRID 1379798 reaction equation
[C:1]([C:3]1[CH:22]=[CH:21][C:6]([C:7]([NH:9][C:10]2[S:11][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:13]([CH3:15])[N:14]=2)=[O:8])=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].[CH3:25]I>CN(C)C=O.Cl>[C:1]([C:3]1[CH:22]=[CH:21][C:6]([C:7]([N:9]=[C:10]2[N:14]([CH3:25])[C:13]([CH3:15])=[C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[S:11]2)=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 748006HCID 748006, compound

Product 1

HCID 4249922HCID 4249922, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent3×

Procedure

Ethyl 2-(4-cyanobenzoylamino)-4-methylthiazole-5-carboxylate (22.07 g) was added to a suspension of 60% oily sodium hydride (3.08 g) in N,N-dimethylformamide (hereinafter referred to as DMF) (300 ml) under ice-cooling, followed by stirring at room temperature for an hour. A solution of methyl iodide (4.8 ml) in DMF (50 ml) was added dropwise to the reaction mixture, followed by further stirring at room temperature for an hour. The reaction mixture was taken up in 3% hydrochloric acid, and the precipitated crystals were collected by filtration, and the resulting crude crystals were recrystallized from a mixture of methylene chloride and methanol to give ethyl 2-(4-cyanobenzoylimino)-3,4-dimethylthiazoline-5-carboxylate (15.97 g).

Workup

  1. temperaturecooling
  2. stirringby further stirring at room temperature for an hour
  3. filtrationthe precipitated crystals were collected by filtration
  4. customthe resulting crude crystals were recrystallized from a mixture of methylene chloride and methanol

Sources & evidence

ORD record
ord-3c8b8831815542e88df04da1e28fbbc0
Source dataset
uspto-grants-1997_09
Patent number
US05672712

Reaction notes

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