Triethylamine → HCID 54190974, compound

HRID 1198830Notes

Reaction equation

HRID 1198830 reaction equation
[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=2)=[N:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C(N(CC)CC)C.ClC(OCC)=O.[N-:34]=[N+:35]=[N-:36].[Na+]>CC(C)=O.O>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:20]=[CH:19][C:15]([C:16]([N:34]=[N+:35]=[N-:36])=[O:17])=[CH:14][CH:13]=2)=[N:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 20536714-(5-pentylpyridin-2-yl)benzoic acid

Product 1

HCID 54190974HCID 54190974, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent3×HCID 962WaterSolvent2×

Procedure

A solution of 2.1 g of p-(5-pentyl-2-pyridyl)benzoic acid in 80 ml of acetone was cooled to 2° C. while stirring and gassing with nitrogen and treated dropwise within 10 minutes with a solution of 2.16 ml of triethylamine in 15 ml of acetone. The reaction mixture was then treated dropwise at 1°-2° C. within 10 minutes with a solution of 1.86 ml of ethyl chloroformate in 8 ml of acetone and stirred at this temperature for a further 30 minutes. Subsequently, a solution of 1.38 g of sodium azide in 8 ml of water was added dropwise to the reaction mixture at 1°-2° C. within 10 minutes and the resulting mixture was stirred for a further 1 hour in an ice-bath. Thereafter, the reaction mixture was poured into 200 ml of water and extracted with diethyl ether. The organic phase was washed with water, dried over sodium sulphate, filtered and freed from solvent. Purification of the resulting light yellowish crystals (2.1 g) by chromatography on 120 g of silica gel with 1 l of methylene chloride gave 2.15 g of p-(5-pentyl-2-pyridyl)benzoic acid azide as a light yellowish paste.

Workup

  1. stirringstirred at this temperature for a further 30 minutes
  2. stirringthe resulting mixture was stirred for a further 1 hour in an ice-bath
  3. extractionextracted with diethyl ether
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customPurification of the resulting light yellowish crystals (2.1 g) by chromatography on 120 g of silica gel with 1 l of methylene chloride

Sources & evidence

ORD record
ord-dc94d4aab95a4184a927b8873dfc678d
Source dataset
uspto-grants-1990_02
Patent number
US04898455

Reaction notes

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