Triethylamine → HCID 23003638, compound

HRID 396289Notes

Reaction equation

HRID 396289 reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(N(CC)CC)C.C(OC(Cl)=O)C.[N-:24]=[N+:25]=[N-:26].[Na+]>CC(C)=O.O>[N:24]([C:4]([C:3]1[C:2]([CH3:1])=[N:10][CH:9]=[CH:8][CH:7]=1)=[O:5])=[N+:25]=[N-:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 6433732-Methylnicotinic acid

Product 1

HCID 23003638HCID 23003638, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-methylnicotinic acid (500 mg, 3.65 mmol) in a mixture of acetone (6.6 mL) and water (3.3 mL) was added triethylamine (1.02 mL, 7.3 mmol). The mixture was cooled to 0° C. in a ice-bath. Ethylchloroformate (0.79 g, 7.3 mmol) was then added and the resulting mixture was stirred for 1.5 hours at 0° C. To the mixture was added sodium azide (0.47 g, 7.3 mmol), and the mixture was stirred for another 1.5 hours. The mixture was concentrated, the residue was diluted with dichloromethane and washed with water. The organic layer was dried over MgSO4 and concentrated to give desired product (390 mg, 62%). 1HNMR (CDCl3) (δ) 8.67 (d, 1H), 8.21 (d, 1H), 7.24 (t, 1H), 2.88 (s, 3H).

Workup

  1. stirringthe mixture was stirred for another 1.5 hours
  2. concentrationThe mixture was concentrated
  3. additionthe residue was diluted with dichloromethane
  4. washwashed with water
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9e5a2980e8484adeaa638153376cefcb
Source dataset
uspto-grants-2003_08
Patent number
US06608077B2

Reaction notes

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