Triethylamine hydrochloride → HCID 178440084, compound

HRID 1600377Notes

Reaction equation

HRID 1600377 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]([C:21]([OH:23])=[O:22])=[C:19]([C:24]([OH:27])([CH3:26])[CH3:25])[N:18]=[C:17]2[CH2:28][CH2:29][CH3:30])=[CH:11][CH:10]=1)#[N:2].[N-:31]=[N+:32]=[N-:33].[Na+].Cl.C(N(CC)CC)C.[OH-].[Na+]>O.C1(C)C=CC=CC=1>[OH:27][C:24]([C:19]1[N:18]=[C:17]([CH2:28][CH2:29][CH3:30])[N:16]([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]3[NH:33][N:32]=[N:31][N:2]=3)=[CH:14][CH:13]=2)[C:20]=1[C:21]([OH:23])=[O:22])([CH3:25])[CH3:26]

Participants

7

Reactant 4

HCID 11130Triethylamine hydrochlorideHCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 193491411-(2'-Cyanobiphenyl-4-yl)methyl-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylic acid

Product 1

HCID 178440084HCID 178440084, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Into a 500-ml flask equipped with a reflux condenser, thermometer and stirrer were placed 43.5 g (0.10 mole) of ethyl ester of 1-(2'-cyanobiphenyl-4-yl)methyl-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylic acid, 19.5 g (0.30 mole) of sodium azide, 41.3 g (0.30 mole) of triethylamine hydrochloride and 206 ml of toluene. The mixture was heated with stirring to a temperature of 95° to 100° C. to undergo a reaction for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature. Then, 35.0 g (0.42 mole) of a 48 wt % aqueous solution of NaOH and 335 ml of water were added. The mixture was fractionated after 2 hours' stirring at room temperature. The aqueous layer was washed and fractionated with the addition of 103 ml of toluene. The aqueous layer was adjusted to a pH of 2 to 3.5 with 36 wt % hydrochloric acid to separate out crystals, which were collected by filtration and dried. The crystals were heated, washed with methanol with stirring, cooled, filtered for collection and dried, giving 32.6 g (0.07 mole) of 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(tetrazole-5-yl)phenyl]phenyl}methylimidazole-5-carboxylic acid (yield 72.4% based on ethyl ester of 1-(2'-cyanobiphenyl-4-yl)methyl-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylic acid). The reaction is illustrated below with chemical formulas. ##STR29##

Workup

  1. customInto a 500-ml flask equipped with a reflux condenser
  2. customthermometer and stirrer were placed
  3. temperatureThe mixture was heated
  4. customa reaction for 24 hours
  5. customAfter completion of the reaction
  6. stirring' stirring at room temperature
  7. washThe aqueous layer was washed
  8. additionfractionated with the addition of 103 ml of toluene
  9. customto separate out crystals, which
  10. filtrationwere collected by filtration
  11. customdried
  12. temperatureThe crystals were heated
  13. washwashed with methanol
  14. stirringwith stirring
  15. temperaturecooled
  16. filtrationfiltered for collection
  17. customdried

Sources & evidence

ORD record
ord-923db83709dd4580bf8ebbdfba30c908
Source dataset
uspto-grants-1998_04
Patent number
US05744612

Reaction notes

Loading…