Dimethylformamide → HCID 23301493, compound

HRID 1952971Notes

Reaction equation

HRID 1952971 reaction equation
[CH3:1][N:2]([C:15]1[NH:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1)[CH2:3][CH2:4][CH2:5][N:6]([CH3:14])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:1][N:2]([C:15]1[N:16]([CH2:29][C:28]2[CH:31]=[CH:32][C:25]([F:24])=[CH:26][CH:27]=2)[C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1)[CH2:3][CH2:4][CH2:5][N:6]([CH3:14])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 96024-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 15480086HCID 15480086, compound

Product 1

HCID 23301493HCID 23301493, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution comprising 1.0 g of N-methyl-N-(benzimidazol-2-yl)-N'-methyl-N'-t-butoxycarbonyl-1,3-propylenediamine, 540 mg of 4-fluorobenzyl chloride, 3 g of potassium carbonate and 20 ml of dimethylformamide, was reacted at room temperature overnight under a stirring condition. Further, it was reacted at a temperature of from 50 to 60° C. for 10 hours. Then, 50 ml of water was added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate (30 ml×3), and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate) to obtain 1.4 g of the above identified compound as a colorless oily substance.

Workup

  1. customwas reacted at room temperature overnight under a stirring condition
  2. customFurther, it was reacted at a temperature of from 50 to 60° C. for 10 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate (30 ml×3)
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate)
  7. customto obtain 1.4 g of the

Sources & evidence

ORD record
ord-ef4bfbcee1584b5abcee936865f79aff
Source dataset
uspto-grants-2000_09
Patent number
US06114369

Reaction notes

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