Hydrochloric Acid → HCID 178442556, compound

HRID 1899419Notes

Reaction equation

HRID 1899419 reaction equation
[CH2:1]([CH:7]([N:10]1[CH:14]=[C:13]([NH:15][C:16](=[O:26])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]([OH:25])=[O:24])[N:12]=[CH:11]1)[C:8]#[N:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C([Sn]([N:40]=[N+:41]=[N-:42])(CCCC)CCCC)CCC.Cl>CO>[OH2:24].[NH:40]1[C:8]([CH:7]([N:10]2[CH:14]=[C:13]([NH:15][C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]([OH:25])=[O:24])=[O:26])[N:12]=[CH:11]2)[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[N:9][N:42]=[N:41]1.[NH:40]1[C:8]([CH:7]([N:10]2[CH:14]=[C:13]([NH:15][C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]([OH:25])=[O:24])=[O:26])[N:12]=[CH:11]2)[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[N:9][N:42]=[N:41]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4984872Tributyltin azideHCID 23373484HCID 23373484, compound

Product 1

HCID 178442556HCID 178442556, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

To 700 mg of α-hexyl-4-[(2-carboxybenzoyl)amino]-1H-imidazole-1-acetonitrile were added 2.0 g of tributyl tin azide. The mixture was heated at 85° C. for 2 days, cooled, and added to 50 ml of methanol previously saturated with hydrogen chloride gas. After stirring for 20 minutes, the solvent was removed in vacuo. The residue was triturated with diethyl ether. The remaining solid was diluted with 100 ml of absolute ethanol and 100 ml of 4N sodium hydroxide. After stirring for two hours, the solution was concentrated in vacuo. The residue was taken up in water and the pH adjusted to 3.7. The aqueous solution was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo. The resulting solid was slurried with diethyl ether and filtered to provide 150 mg of the desired titled product, m.p. 120°-121° C.

Workup

  1. temperaturecooled
  2. customthe solvent was removed in vacuo
  3. customThe residue was triturated with diethyl ether
  4. additionThe remaining solid was diluted with 100 ml of absolute ethanol and 100 ml of 4N sodium hydroxide
  5. stirringAfter stirring for two hours
  6. concentrationthe solution was concentrated in vacuo
  7. extractionThe aqueous solution was extracted with ethyl acetate
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. filtrationfiltered

Sources & evidence

ORD record
ord-8398d4f8ec684681807097f6204b4c23
Source dataset
uspto-grants-1996_11
Patent number
US05571925

Reaction notes

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