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

HRID 59875

반응식

HRID 59875 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

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]+).

후처리

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

출처 및 근거

ORD 기록
ord-d4afa4a325cf4cd8884cd104d4f8dc13
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440964B2

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