Triethylamine → 2-methyl-4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzoyl azide

HRID 59881

반응식

HRID 59881 반응식
[CH3:1][C:2]1[CH:10]=[C:9]([C:11]2[N:15]=[CH:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(N(CC)CC)C.P([N:50]=[N+:51]=[N-:52])(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1>C(O)(C)C>[CH3:1][C:2]1[CH:10]=[C:9]([C:11]2[N:15]=[CH:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:24])[F:25])=[CH:18][CH:17]=3)[N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([N:50]=[N+:51]=[N-:52])=[O:5]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 712093312-methyl-4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzoic acid

생성물 1

HCID 866758162-methyl-4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzoyl azide수율 67%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

To 2-methyl-4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzoic acid (0.412 g, 1.134 mmol) in a 100 mL round-bottomed flask equipped with a stir bar under N2 was added isopropyl alcohol (11 mL), triethylamine (0.205 ml, 1.474 mmol) and diphenyl phosphorazidate (0.319 ml, 1.474 mmol). The reaction was stirred at room temperature overnight. The resultant solid was filtered, washed with isopropyl alcohol followed by hexanes and dried under vacuum providing the title compound as a white solid (0.294 g, 0.757 mmol, 67%): 1H NMR (300 MHz, CDCl3) δ 8.60 (s, 1H), 8.13 (s, 1H), 8.11-8.02 (m, 2H), 7.84-7.77 (m, 2H), 7.40 (d, J=8.6 Hz, 2H), 2.74 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −58.02; ESIMS m/z 389 ([M+H]+).

후처리

  1. filtrationThe resultant solid was filtered
  2. washwashed with isopropyl alcohol
  3. customdried under vacuum

출처 및 근거

ORD 기록
ord-f0b0861a78864e13ac74a01537dd98cf
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440964B2

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