4-Amino-1,2,4-triazole → 4-(4H-1,2,4-Triazol-4-ylamino)-2-bromobenzonitrile

HRID 82778

반응식

HRID 82778 반응식
[N:1]1[N:2]=[CH:3][N:4]([NH2:6])[CH:5]=1.CC([O-])(C)C.[K+].F[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([Br:22])[CH:15]=1.OS([O-])(=O)=O.[K+]>CS(C)=O>[N:1]1[N:2]=[CH:3][N:4]([NH:6][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([Br:22])[CH:15]=2)[CH:5]=1

참가 물질

6

반응물 4

HCID 114324-Amino-1,2,4-triazoleHCID 1189392-Bromo-4-fluorobenzonitrileHCID 516920Potassium bisulfateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 682284934-(4H-1,2,4-Triazol-4-ylamino)-2-bromobenzonitrile

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution of 4H-1,2,4-triazol-4-amine (4.204 g, 50.0 mmol) in DMSO (50 mL) was added KOtBu (5.51 g, 50.0 mmol). The mixture was stirred for 0.5 hours at room temperature before 4-fluoro-2-bromobenzonitrile (5.00 g, 25.0 mmol) was added and stirring was continued for 1 hour. The mixture was poured into crushed ice and neutralized with 2M KHSO4 solution. The precipitate was filtered off and recrystallised from MeOH to give CAB05094 (4.82 g, 73%) as a light yellow crystalline solid. Mp. 234-236° C.; 1H NMR (400 MHz, DMSO-d6) δ 6.66 (dd, J=8.6, 2.4 Hz, 1H), 6.79 (d, J=2.4 Hz, 1H), 7.78 (d, J=8.6 Hz, 1H), 8.86 (s, 2H), 10.45 (s, 1H); 13C NMR (100.6 MHz, DMSO-d6) δ 105.0, 111.5, 115.4, 117.8, 126.0, 136.2, 143.9, 151.8; LRMS (APCI−): m/z 261.8 (100%, [C9H579BrN5]−), 263.8 (90%, [C9H581BrN5]−); HRMS (ES+) calcd for C9H779BrN5 [M+H]+: 263.9879. found 263.9870;

후처리

  1. additionwas added
  2. additionThe mixture was poured
  3. custominto crushed ice
  4. filtrationThe precipitate was filtered off
  5. customrecrystallised from MeOH
  6. customto give CAB05094 (4.82 g, 73%) as a light yellow crystalline solid

출처 및 근거

ORD 기록
ord-797b3653e6ea487ca414cf3392dff835
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846737B2

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