Triethylamine → 4-(5-(4-(Perfluoroethoxy)phenyl)-1,3,4-oxadiazol-2-yl)benzoyl azide

HRID 59875

Reaction equation

HRID 59875 reaction equation
[F:1][C:2]([F:28])([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][C:17]([C:19]3[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=3)=[N:16][N:15]=2)=[CH:10][CH:9]=1)[C:3]([F:6])([F:5])[F:4].C(N(CC)CC)C.P([N:52]=[N+:53]=[N-:54])(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1>C(O)(C)C>[F:28][C:2]([F:1])([O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[O:18][C:17]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([N:52]=[N+:53]=[N-:54])=[O:24])=[CH:21][CH:20]=3)=[N:16][N:15]=2)=[CH:12][CH:13]=1)[C:3]([F:5])([F:4])[F:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 866758104-(5-(4-(Perfluoroethoxy)phenyl)-1,3,4-oxadiazol-2-yl)benzoic acid

Product 1

HCID 866758114-(5-(4-(Perfluoroethoxy)phenyl)-1,3,4-oxadiazol-2-yl)benzoyl azideYield 63.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 4-(5-(4-(perfluoroethoxy)phenyl)-1,3,4-oxadiazol-2-yl)benzoic acid (217 mg, 0.54 mmol) in isopropanol (5.4 mL) was added triethylamine (0.09 mL, 0.65 mmol) and diphenyl phosphorazidate (0.13 mL, 0.60 mmol) and the reaction was stirred at room temperature for 16 hours. The white precipitate that had formed was filtered and dried in a vacuum oven to provide 4-(5-(4-(perfluoroethoxy)phenyl)-1,3,4-oxadiazol-2-yl)benzoyl azide as a white solid (145 mg, 63%): mp 140° C. (dec); 1H NMR (400 MHz, DMSO-d6) δ 8.32 (m, 4H), 8.24-8.17 (m, 2H), 7.68 (d, J=8.9 Hz, 2H); 19F NMR (376 MHz, DMSO-d6) δ −85.25, −86.89; ESIMS m/z 426 ([M+H]+).

Workup

  1. customThe white precipitate that had formed
  2. filtrationwas filtered
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-d4afa4a325cf4cd8884cd104d4f8dc13
Source dataset
uspto-grants-2016_09
Patent number
US09440964B2

Linked notes

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