Hydrochloric Acid → Benzimidazole, 5,6-dichloro-2-pentafluoroethyl-

HRID 230458

반응식

HRID 230458 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH2:9])=[CH:6][C:7]=1[Cl:8].[F:11][C:12]([F:20])([C:16]([F:19])([F:18])[F:17])[C:13](O)=O.Cl.C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]2[NH:9][C:13]([C:12]([F:20])([F:11])[C:16]([F:19])([F:18])[F:17])=[N:10][C:4]=2[CH:3]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 62356Pentafluoropropionic acidHCID 792974,5-Dichloro-1,2-phenylenediamineHCID 516892Sodium Bicarbonate

생성물 1

HCID 59446Benzimidazole, 5,6-dichloro-2-pentafluoroethyl-

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
108 °C

실험 절차

4,5-Dichloro-benzene-1,2-diamine (2.01 g; 11.4 mmoles) and 2,2,3,3,3-pentafluoro-propionic acid (1.80 mL; 17.3 mmoles) were suspended in 6N HCl (10 mL; 60 mmoles) under a nitrogen atmosphere. The reaction was stirred vigorously and heated to 108° C. for 18 hrs, then cooled to room temperature. The reaction was diluted with water (60 mL) and with ethyl acetate (60 mL), then sodium bicarbonate (7.59 g; 90.3 mmoles) was added slowly and in portions to quench the reaction. The aqueous layer was separated and extracted with ethyl acetate (3×30 mL). The extracts were combined, washed with water (30 mL) and brine (30 mL), then dried over Na2SO4. The filtrate was concentrated in vacuo to yield a crude brown solid which was then purified by column chromatography (SiO2; 100% CH2Cl2) to yield the title compound as a light tan solid.

후처리

  1. temperaturecooled to room temperature
  2. customto quench
  3. customthe reaction
  4. customThe aqueous layer was separated
  5. extractionextracted with ethyl acetate (3×30 mL)
  6. washwashed with water (30 mL) and brine (30 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto yield a crude brown solid which
  10. customwas then purified by column chromatography (SiO2; 100% CH2Cl2)

출처 및 근거

ORD 기록
ord-b4d0e34621534fda97069e04d93e8446
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566733B2

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