Sodium Methoxide → HCID 86758336, compound

HRID 2228848Notes

Reaction equation

HRID 2228848 reaction equation
C[O-].[Na+].[CH3:4][O:5][N:6]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]([O:20][N:21]=[CH:22][C:23](=[N:28][O:29][CH3:30])[CH2:24][C:25]([CH3:27])=[CH2:26])[CH3:19])[C:8]([NH:10][CH3:11])=[O:9]>CN(C=O)C>[CH3:4][O:5][N:6]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]([O:20][N:21]=[CH:22][C:23](=[N:28][O:29][CH3:30])[CH:24]=[C:25]([CH3:26])[CH3:27])[CH3:19])[C:8]([NH:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86758337HCID 86758337, compound

Product 1

HCID 86758336HCID 86758336, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
30 °C

Procedure

34.7 g of solid sodium methoxide in 250 ml of DMF were stirred at 23° C. for 3 hours and 120 g of the amide from Example 6 in 250 ml of DMF were then added dropwise (temperature increase to up to 30° C.). The mixture was subsequently stirred at 23° C. for 12 hours and then worked-up as in Example 6. This gave 108 g of the title compound as a colorless solid which, according to NMR, GC and HPLC analysis, contains approximately 10% of the starting material (Example 6).

Sources & evidence

ORD record
ord-11b58b8fcc2b4beaad61c213ded23c1a
Source dataset
uspto-grants-2002_07
Patent number
US06417388B1

Reaction notes

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