Dimethylformamide → HCID 58424909, compound

HRID 2409393Notes

Reaction equation

HRID 2409393 reaction equation
CN(C)C=O.[Cl:6][C:7]1[N:23]=[CH:22][CH:21]=[CH:20][C:8]=1[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)=[O:10].[H-].[Na+].[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Cl)=[CH:30][CH:29]=1>O.ClCCl>[Cl:6][C:7]1[N:23]=[CH:22][CH:21]=[CH:20][C:8]=1[C:9]([N:11]([CH2:32][C:31]1[CH:34]=[CH:35][C:28]([O:27][CH3:26])=[CH:29][CH:30]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)=[O:10]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 3343465HCID 3343465, compound

Product 1

HCID 58424909HCID 58424909, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N,N-Dimethylformamide was added to the compound (972.4 mg, 3.1736 mmol) prepared in step 1 and the mixture was cooled to 0° C. Sodium hydride (380 mg, 9.52 mmol) was slowly added and the resulting mixture stirred at 0° C. for 20 minutes. p-Methoxybenzyl chloride (0.646 ml, 4.76 mmol) was added at 0° C. and the mixture stirred for 3 hours at room temperature. Once the reaction was completed, dichloromethane and water was added, the organic layer was dried over magnesium sulfate, and the solvent was concentrated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=2.5:1) to obtain the title compound (1.01 g, yield: 84%, ivory oil).

Workup

  1. stirringthe mixture stirred for 3 hours at room temperature
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. concentrationthe solvent was concentrated under reduced pressure
  4. customThe residue was purified by flash column chromatography (hexane:ethyl acetate=2.5:1)

Sources & evidence

ORD record
ord-bf969fd664d94990925c72c39e13b68a
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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