N-Hydroxysuccinimide → HCID 20134099, compound

HRID 580499Notes

Reaction equation

HRID 580499 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14]([CH:18]=1)[C:15]([OH:17])=[O:16]>C(OCC)(=O)C>[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14]([CH:18]=1)[C:15]([OH:17])=[O:16].[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8]

Participants

4

Reactant 2

HCID 80170N-HydroxysuccinimideHCID 887075-Bromonicotinic acid

Product 1

HCID 20134099HCID 20134099, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.77 g of N,N-dicyclohexylcarbodiimide are added to 1 g of N-hydroxysuccinimide and 5.2 g of 5-bromonicotinic acid dissolved in 100 ml of abs. ethyl acetate at 50° C. The reaction mixture is stirred at room temperature for 4 hours, then cooled to 5° C. and the precipitated white crystals are filtered off. The filtrate is evaporated under reduced pressure and the residue is recrystallized from ethanol.

Workup

  1. dissolutiondissolved in 100 ml of abs
  2. customat 50° C
  3. temperaturecooled to 5° C.
  4. filtrationthe precipitated white crystals are filtered off
  5. customThe filtrate is evaporated under reduced pressure
  6. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-475b9e9d3b274b61bd435a08ae6755c5
Source dataset
uspto-grants-1988_06
Patent number
US04753949

Reaction notes

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