Triethylamine hydrochloride → HCID 178440084, compound

HRID 1637363Notes

Reaction equation

HRID 1637363 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

Conditions

Temperature
97.5 °C

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. temperaturethe reaction mixture was cooled to room temperature
  7. stirring' stirring at room temperature
  8. washThe aqueous layer was washed
  9. additionfractionated with the addition of 103 ml of toluene
  10. customto separate out crystals, which
  11. filtrationwere collected by filtration
  12. customdried
  13. temperatureThe crystals were heated
  14. washwashed with methanol
  15. stirringwith stirring
  16. temperaturecooled
  17. filtrationfiltered for collection
  18. customdried

Sources & evidence

ORD record
ord-e4829d7eea2e4f4e900ca4c0584ff59d
Source dataset
uspto-grants-2000_03
Patent number
US06040454

Reaction notes

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