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

HRID 230457

反応式

HRID 230457 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:12])[C:6]([NH2:11])=[CH:7][C:8]=1[O:9][CH3:10].[F:13][C:14]([F:21])([F:20])[CH:15]([OH:19])[C:16](O)=O.Cl.C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C>[CH3:10][O:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[NH:12][C:16]([CH:15]([OH:19])[C:14]([F:21])([F:20])[F:13])=[N:11][C:6]=2[CH:7]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1529391,2-Diamino-4,5-dimethoxybenzeneHCID 2448963,3,3-Trifluoro-2-hydroxypropanoic acidHCID 516892Sodium Bicarbonate

生成物 1

HCID 596822851-(5,6-Dimethoxy-1H-benzoimidazol-2-yl-)2,2,2-trifluoro-ethanol

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
108 °C

実験手順

4,5-Dimethoxy-benzene-1,2-diamine (2.02 g; 12.0 mmoles) and 3,3,3-trifluoro-2-hydroxy-propionic acid (2.67 g; 18.5 mmoles) were suspended in 6N HCl (5 mL; 30 mmoles) and water (4 mL) 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 (40 mL) and with ethyl acetate (40 mL), then sodium bicarbonate (3.84 g; 46.0 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 (40 mL), then dried over Na2SO4. The filtrate was concentrated in vacuo to yield a crude dark orange solid which was then purified by column chromatography (SiO2; 30% ethyl acetate/CH2Cl2) to yield the title compound as a bright orange solid.

後処理

  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 (40 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto yield a crude dark orange solid which
  10. customwas then purified by column chromatography (SiO2; 30% ethyl acetate/CH2Cl2)

出典と根拠

ORDレコード
ord-01614343eb5f40aca2fbae0c5f89cb56
出典データセット
uspto-grants-2009_07
特許番号
US07566733B2

関連ノート

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