Hydrochloric Acid → 1-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanol

HRID 1360966

반응식

HRID 1360966 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:19])([F:18])[CH:13]([OH:17])[C:14](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:14]([CH:13]([OH:17])[C:12]([F:19])([F:18])[F:11])=[N:10][C:4]=2[CH:3]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 792974,5-Dichloro-1,2-phenylenediamineHCID 2448963,3,3-Trifluoro-2-hydroxypropanoic acidHCID 516892Sodium Bicarbonate

생성물 1

HCID 116377781-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanol

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
108 °C

실험 절차

4,5-Dichloro-benzene-1,2-diamine (8.50 g; 48.0 mmoles) and 3,3,3-trifluoro-2-hydroxy-propionic acid (10.59 g; 73.52 mmoles) were suspended in 6N HCl (19 mL; 114 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 (200 mL) and with ethyl acetate (200 mL), then sodium bicarbonate (6.05 g; 72.0 mmoles) was added slowly and in portions to quench the reaction. The aqueous layer was separated and extracted with ethyl acetate (3×80 mL). The extracts were combined, washed with water (60 mL) and brine (60 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; 30% ethyl acetate/CH2Cl2) to yield the title compound as a brown solid.

후처리

  1. temperaturecooled to room temperature
  2. customto quench
  3. customthe reaction
  4. customThe aqueous layer was separated
  5. extractionextracted with ethyl acetate (3×80 mL)
  6. washwashed with water (60 mL) and brine (60 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; 30% ethyl acetate/CH2Cl2)

출처 및 근거

ORD 기록
ord-fe20e866012047b9b2a4eb102d51d18e
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879895B2

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