Acetic Acid → HCID 9848039, compound

HRID 1840543Notes

Reaction equation

HRID 1840543 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([NH:16][CH2:17][CH2:18][NH2:19])(=[O:15])=[O:14])[CH:7]=[CH:6]2.[N:20]1([C:25]2[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=2)[CH:24]=[CH:23][N:22]=[CH:21]1.[C:33]([OH:36])(=O)[CH3:34].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:17][CH2:18][N:19]([CH2:29][C:28]3[CH:31]=[CH:32][C:25]([N:20]4[CH:24]=[CH:23][N:22]=[CH:21]4)=[CH:26][CH:27]=3)[C:33](=[O:36])[CH2:34]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7365304-(1H-imidazol-1-yl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 23447437239074-31-8

Product 1

HCID 9848039HCID 9848039, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(6-chloronaphthalene-2-sulfonyl)ethylenediamine hydrochloride (321 mg) and 4-(1H-imidazol-1-yl)benzaldehyde (172 mg) in methanol (10 ml) was added acetic acid (300 mg), and the mixture was stirred at room temperature for 1 hour. To the mixture was added, under ice-cooling, sodium triacetoxyborohydride (318 mg), and the mixture was stirred at room temperature for 5 hours. The reaction solution was concentrated, and the residue was dissolved in ethyl acetate. The solution was washed with sodium bicarbonate solution and brine, and dried, and to the solution was added triethylamine (700 mg) and then was added chloroacetyl chloride (300 mg). The mixture was stirred at room temperature for 30 minutes. The reaction solution was washed with sodium bicarbonate solution and brine, dried and concentrated. The residue was dissolved in DMF (20 ml), and to the solution was added potassium carbonate (150 mg). The mixture was stirred at 90 C for 2 hours. The reaction solution was concentrated, and the residue was dissolved in ethyl acetate, washed with water and brine, dried and concentrated. The residue was purified with column chromatography (ethyl acetate) and recrystallized from ethyl acetate to give colorless crystals of the title compound (177 mg).

Workup

  1. additionTo the mixture was added, under ice-
  2. temperaturecooling
  3. concentrationThe reaction solution was concentrated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe solution was washed with sodium bicarbonate solution and brine
  6. customdried
  7. additionto the solution was added triethylamine (700 mg)
  8. additionwas added chloroacetyl chloride (300 mg)
  9. stirringThe mixture was stirred at room temperature for 30 minutes
  10. washThe reaction solution was washed with sodium bicarbonate solution and brine
  11. customdried
  12. concentrationconcentrated
  13. dissolutionThe residue was dissolved in DMF (20 ml)
  14. additionto the solution was added potassium carbonate (150 mg)
  15. stirringThe mixture was stirred at 90 C for 2 hours
  16. concentrationThe reaction solution was concentrated
  17. dissolutionthe residue was dissolved in ethyl acetate
  18. washwashed with water and brine
  19. customdried
  20. concentrationconcentrated
  21. customThe residue was purified with column chromatography (ethyl acetate)
  22. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-418dc594830943baa4ff8ac2e13f0c6c
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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