Dimethylformamide → Sodium 2-[[[5-[[(2,5-dioxo-1-pyrolidinyl)oxy]carbonyl]-2-pyridinyl] hydrazono]methyl]-benzenesulfonate

HRID 2228528Notes

Reaction equation

HRID 2228528 reaction equation
[Na+:1].[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([O-:13])(=[O:12])=[O:11])=O.N(C1N=CC=CC=1[C:18](O)=[O:19])N.[OH:25][N:26]1[C:30](=[O:31])[CH2:29][CH2:28][C:27]1=[O:32].C1([N:39]=[C:40]=[N:41][CH:42]2[CH2:47][CH2:46][CH2:45]CC2)CCCCC1.C[N:49](C)C=O>CO>[O:32]=[C:27]1[CH2:28][CH2:29][C:30](=[O:31])[N:26]1[O:25][C:18]([C:47]1[CH:46]=[CH:45][C:40]([NH:39][N:49]=[CH:2][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:10]([O-:13])(=[O:12])=[O:11])=[N:41][CH:42]=1)=[O:19].[Na+:1]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 585323Hydrazinonicotinic acidHCID 3794540Sodium o-formylbenzenesulfonate

Product 1

HCID 59642097Sodium 2-[[[5-[[(2,5-dioxo-1-pyrolidinyl)oxy]carbonyl]-2-pyridinyl] hydrazono]methyl]-benzenesulfonate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-formylbenzenesulfonic acid sodium salt (13.6 g) in dimethylformamide (400 mL) was added 2-hydrazinonicotinic acid (10.0 g) and the mixture stirred for three hours. N-hydroxysuccinimide (7.52 g) and dicyclohexylcarbodiimide (27.6 g) were added to the reaction and it was stirred for 16 hours. The mixture was filtered through Celite and the filtrate concentrated under vacuum to a thick oil. This was triturated with ethyl acetate to afford a solid which was filtered to afford crude product (32.8 g). The solids were refluxed in hot methanol for 5 hours, filtered, washed with methanol, and dried under vacuum to afford Sodium 2-[[[5-[[(2,5-dioxo-1-pyrolidinyl)oxy]carbonyl]-2-pyridinyl]hydrazono]methyl]-benzenesulfonate (21.2 g) as a pale yellow solid. NMR (DMSO-d6): 2.88, s (4H); 7.36, m (3H); 7.79, d of d (1H); 8.10, m (2H); 8.79, t (1H); 9.16, s (1H); 11.90, s (1H).

Workup

  1. stirringwas stirred for 16 hours
  2. filtrationThe mixture was filtered through Celite
  3. concentrationthe filtrate concentrated under vacuum to a thick oil
  4. customThis was triturated with ethyl acetate
  5. customto afford a solid which
  6. filtrationwas filtered
  7. customto afford crude product (32.8 g)
  8. filtrationfiltered
  9. washwashed with methanol
  10. customdried under vacuum

Sources & evidence

ORD record
ord-95bb91ba427947f6bec2e3f9a747523e
Source dataset
uspto-grants-2002_07
Patent number
US06416733B1

Reaction notes

Loading…