1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86756985, compound

HRID 1066341Notes

Reaction equation

HRID 1066341 reaction equation
[CH3:1][N:2]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[Cl:23])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([OH:8])=O.[CH2:24]([S:29]([NH2:32])(=[O:31])=[O:30])[CH2:25][CH2:26][CH2:27][CH3:28].N12CCCN=C1CCCCC2>CN(C)C=O>[CH2:24]([S:29]([NH:32][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:11]([N+:12]([O-:14])=[O:13])=[C:3]([N:2]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])[CH3:1])[CH:4]=1)(=[O:31])=[O:30])[CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 109206961-PentanesulfonamideHCID 21198588HCID 21198588, compound

Product 1

HCID 86756985HCID 86756985, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N′-carbonyldiimidazole (0.776 g) was added to a mixture of 0.85 g of 3-(N-methyl-2,4-dichlorobenzylamino)-4-nitrobenzoic acid and 10 ml N,N-dimethylformamide at room temperature, and the mixture was stirred for 1 hour. 1-Pentanesulfonamide (0.724 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.729 g) were then added thereto, and the resulting mixture was stirred at 100° C. for 21 hours. The mixture was concentrated, and the resulting residue was dissolved in ethyl acetate. The organic layer was washed with water, concentrated, and purified by silica-gel column chromatography (eluent: a mixture of hexane and ethyl acetate at a ratio of 1:1 to 0:1). The desired fractions were collected and concentrated. The concentrate was re-dissolved in ethyl acetate, washed twice with diluted hydrochloric acid and subsequently with a solution of sodium hydrogen carbonate. The organic layer was dried and concentrated to give 0.605 g of N-(n-pentanesulfonyl)-3-(N-methy-2,4-dichlorobenzylamino)-4-nitrobenzamide. This product was used immediately in the next reaction step.

Workup

  1. stirringthe resulting mixture was stirred at 100° C. for 21 hours
  2. concentrationThe mixture was concentrated
  3. dissolutionthe resulting residue was dissolved in ethyl acetate
  4. washThe organic layer was washed with water
  5. concentrationconcentrated
  6. custompurified by silica-gel column chromatography (eluent
  7. additiona mixture of hexane and ethyl acetate at a ratio of 1:1 to 0:1)
  8. customThe desired fractions were collected
  9. concentrationconcentrated
  10. dissolutionThe concentrate was re-dissolved in ethyl acetate
  11. washwashed twice with diluted hydrochloric acid and subsequently with a solution of sodium hydrogen carbonate
  12. customThe organic layer was dried
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-13166e5c2d304a0f8e63771f4c73d83a
Source dataset
uspto-grants-2001_06
Patent number
US06242474B1

Reaction notes

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