HCID 4447362, 화합물 → 3-(1H-benzimidazol-2-yl)-4-chloroaniline

HRID 1618940노트

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HRID 1618940 반응식
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O)=O>C1(C)C=CC=CC=1.C(O)(=O)C.[Fe]>[NH:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:13]=[C:4]1[C:3]1[CH:16]=[C:17]([NH2:20])[CH:18]=[CH:19][C:2]=1[Cl:1]

참가 물질

5

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HCID 4447362HCID 4447362, 화합물

생성물 1

HCID 2788313-(1H-benzimidazol-2-yl)-4-chloroaniline수율 49.7%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 176Acetic Acid용매HCID 1140Toluene용매

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온도
125 °C

실험 절차

Iron powder (15.42 g, 280 mmol) was added to a solution of amide 1 (15.00 g, 46.7 mmol) in toluene (125 ml) and acetic acid (60 nil). The mixture was heated at 125° C. for about 1 h (completion of the reaction was monitored by LCMS) and the resulting crude mixture was filtered through a cotton wool plug (to remove iron particles). The crude solution was evaporated to dryness, diluted with EtOAc, washed with saturated NaHCO3 then brine, dried over MgSO4, filtered, and concentrated at reduced pressure. The resulting brown solid was redissolved in CH2Cl2 and few drops of hexane were added to form a solid which was isolated by filtration to give 2 (5.66 g, 42%) as a beige solid: 1H NMR (CD3OD) δ 7.64 (broad s, 2H), 7.30-7.26 (m, 3H), 7.13 (app d, 1H), 6.84 (dd, 1H); MS (ES, positive mode): 244 [M++1].

후처리

  1. filtrationwas filtered through a cotton wool plug (to remove iron particles)
  2. customThe crude solution was evaporated to dryness
  3. additiondiluted with EtOAc
  4. washwashed with saturated NaHCO3
  5. dry with materialbrine, dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure
  8. dissolutionThe resulting brown solid was redissolved in CH2Cl2
  9. additionfew drops of hexane were added
  10. customto form a solid which
  11. customwas isolated by filtration

출처 및 근거

ORD 기록
ord-6376232c5f844bbd86858bf177d15412
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772275B2

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