Triethylamine → HCID 178444275, compound

HRID 247685Notes

Reaction equation

HRID 247685 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([OH:26])=O)=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH:4]=[CH2:5].C(N(CC)CC)C.ClC(OCC)=O.[N-:40]=[N+:41]=[N-:42].[Na+]>CC(C)=O.O>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([N:40]=[N+:41]=[N-:42])=[O:26])=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH:4]=[CH2:5]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 178444278HCID 178444278, compound

Product 1

HCID 178444275HCID 178444275, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent3×HCID 962WaterSolvent2×

Conditions

Temperature
2 °C

Procedure

A mixture of 10.3 g of 4'-[trans-4-(4-pentenyl)cyclohexyl]-4-biphenylcarboxylic acid and 300 ml of acetone was cooled to 2° C. while stirring and gassing with nitrogen, treated dropwise within 10 minutes with a solution of 8.2 ml of triethylamine in 58 ml of acetone and stirred for a further 5 minutes. Thereafter, the mixture was treated dropwise at 0°-2° C. within 10 minutes with a solution of 7.1 ml of ethyl chloroformate in 29 ml of acetone. The mixture was stirred for a further 30 minutes at 0°-2° C. and treated dropwise within 10 minutes with a solution of 5.25 g of sodium azide in 29 ml of water. The reaction mixture was stirred for a further 2.25 hours while cooling with an ice-bath, then poured into 1 l of water and extracted once with 1 l of diethyl ether and once with 500 ml of diethyl ether. The ether phases were washed with water, dried over sodium sulphate, filtered and concentrated. The beige crystalline residue (12.2 g) was separated by chromatography on silica gel with methylene chloride, whereby 9.9 g (89.5%) of 4'(trans-4-(4-pentenyl)cyclohexyl]-4-biphenylcarboxylic acid azide were obtained as colourless crystals.

Workup

  1. stirringstirred for a further 5 minutes
  2. stirringThe mixture was stirred for a further 30 minutes at 0°-2° C.
  3. stirringThe reaction mixture was stirred for a further 2.25 hours
  4. temperaturewhile cooling with an ice-bath
  5. extractionextracted once with 1 l of diethyl ether and once with 500 ml of diethyl ether
  6. washThe ether phases were washed with water
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe beige crystalline residue (12.2 g) was separated by chromatography on silica gel with methylene chloride

Sources & evidence

ORD record
ord-cd7f927e3cc04c2d845a7f6be40fbe3c
Source dataset
uspto-grants-1987_11
Patent number
US04709030

Reaction notes

Loading…