Acetic Acid → HCID 178500257, compound

HRID 2174350Notes

Reaction equation

HRID 2174350 reaction equation
COC(=O)[CH:4]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]C.[CH3:35]CN(CC)CC.[CH3:42][C:43]([OH:45])=[O:44].[N-:46]=[N+:47]=[N-:48].[Na+].Cl>O.CN(C=O)C>[CH3:35][O:44][C:43](=[O:45])[CH2:42][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][O:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:27]=[CH:28][C:29]([C:32]3[NH:33][N:48]=[N:47][N:46]=3)=[CH:30][CH:31]=2)=[CH:24][CH:25]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 33557Sodium AzideHCID 66978124HCID 66978124, compound

Product 1

HCID 178500257HCID 178500257, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of (4′-cyanobiphenyl-4-yloxy)hexadecanoic acid methyl ester (2.75 g, 5.93 mmol), DMF (7.0 ml), NEt3 (4.0 ml, 28.9 mmol), AcOH (1.75 ml, 29.1 mmol), and NaN3 (2.50 g, 38.5 mmol) was stirred at 140° C. After 17 h water (50 ml) and 1N HCl (50 ml) were added, followed by acidification with conc. HCl (approx 2 ml). The product was filtered and recrystallized from MeCN/PhMe (approx 60+60 ml). Filtration and drying under reduced pressure yielded 2.87 g (96%) of 16-(4′-(5-tetrazolyl)biphenyl-4-yloxy)hexadecanoic acid methyl ester.

Workup

  1. filtrationThe product was filtered
  2. customrecrystallized from MeCN/PhMe (approx 60+60 ml)
  3. filtrationFiltration
  4. customdrying under reduced pressure

Sources & evidence

ORD record
ord-8e083b50f2ba40d186f020834f6f189e
Source dataset
uspto-grants-2015_06
Patent number
US09061067B2

Reaction notes

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