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

HRID 59875

反応式

HRID 59875 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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]+).

後処理

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

出典と根拠

ORDレコード
ord-d4afa4a325cf4cd8884cd104d4f8dc13
出典データセット
uspto-grants-2016_09
特許番号
US09440964B2

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