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

HRID 1977731Notes

Reaction equation

HRID 1977731 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][CH:9]=[C:10]([C:12]([OH:14])=O)[N:11]=2)[CH:2]=1.CN(C)C.ClC(OCC(C)C)=O.[N-:27]=[N+:28]=[N-:29].[Na+]>ClCCl.C(Cl)(Cl)Cl.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][CH:9]=[C:10]([C:12]([N:27]=[N+:28]=[N-:29])=[O:14])[N:11]=2)[CH:2]=1

Participants

7

Reactant 4

HCID 1146TrimethylamineHCID 33557Sodium AzideHCID 62365Isobutyl chloroformateHCID 7365132-(3-Pyridyl)thiazole-4-carboxylic acid

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 18399249Chloroform dichloromethaneSolvent

Procedure

A suspension of 2-(3-pyridyl)-thiazole-4-carboxylic acid (0.824 g, 4 mmol) in dichloromethane-chloroform (30 ml-15 ml) was treated with trimethylamine (0.75 ml, 0.5 g, 5 mmol) and then iso-butyl 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-a5094003616244a199b253b8274a0e5c
Source dataset
uspto-grants-2001_05
Patent number
US06235758B1

Reaction notes

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