Water → 2-(3-Pyridinyl)-4-thiazolylcarbonylazide

HRID 989170Notes

Reaction equation

HRID 989170 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2(C(O)=O)[NH:11][CH:10]=[CH:9][S:8]2)[CH:2]=1.C([N:17]([CH2:20]C)CC)C.[N-]=[N+:23]=[N-:24].[Na+].[OH2:26]>ClCCl.C(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][CH:9]=[C:10]([C:20]([N:17]=[N+:23]=[N-:24])=[O:26])[N:11]=2)[CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 33557Sodium AzideHCID 691802632-(3-Pyridyl)-thiazolecarboxylic acid

Product 1

HCID 187718652-(3-Pyridinyl)-4-thiazolylcarbonylazideYield 40%

Reagents, catalysts & solvents 1

HCID 18399249Chloroform dichloromethaneSolvent

Procedure

A suspension of 2-(3-pyridyl)-thiazolecarboxylic acid (0.824 g, 4 mmol) in dichloromethane-chloroform (30 ml-15 ml) was treated with triethylamine (0.75 ml, 0.5 g, 5 mmol) and then dibutyl chloroformate (0.65 ml, 0.68 g, 5 mmol). After 1 h the mixture was evaporated to dryness and the residue suspended in THF (30 ml) and a solution of sodium azide (0.46 g, 7 mmol) in water (10 ml) was added. After 1 h, the mixture was concentrated (rotary evaporator) and partitioned between dichloromethane and brine. The organic extract was washed with half-saturated brine, dried, and evaporated. Trituration with petroleum ether, filtration, and drying in vacuo (CAUTION—no heating) afforded the title compounds as a brown solid (0.37 g, 40%).

Workup

  1. customAfter 1 h the mixture was evaporated to dryness
  2. concentrationthe mixture was concentrated
  3. custom(rotary evaporator)
  4. custompartitioned between dichloromethane and brine
  5. extractionThe organic extract
  6. washwas washed with half-saturated brine
  7. customdried
  8. customevaporated
  9. filtrationTrituration with petroleum ether, filtration
  10. customdrying in vacuo (CAUTION—no heating)

Sources & evidence

ORD record
ord-b31ca04aedc04f8c9576af47f52ccc69
Source dataset
uspto-grants-2003_10
Patent number
US06638953B2

Reaction notes

Loading…