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

HRID 230456

反応式

HRID 230456 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:14])[C:7]([NH2:13])=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])([O-:3])=[O:2].[F:15][C:16]([F:23])([F:22])[CH:17]([OH:21])[C:18](O)=O.Cl.C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C>[N+:1]([C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:7]2[NH:13][C:18]([CH:17]([OH:21])[C:16]([F:23])([F:22])[F:15])=[N:14][C:6]=2[CH:5]=1)([O-:3])=[O:2]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 2448963,3,3-Trifluoro-2-hydroxypropanoic acidHCID 516892Sodium BicarbonateHCID 44419034,5-Dinitrobenzene-1,2-diamine

生成物 1

HCID 596822791-(5,6-Dinitro-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-Dinitro-benzene-1,2-diamine (2.01 g; 10.2 mmoles) and 3,3,3-trifluoro-2-hydroxy-propionic acid (2.22 g; 15.4 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 (3.79 g; 45.0 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 brown solid which was then purified by column chromatography (SiO2; 30% ethyl acetate/CH2Cl2) to yield the title compound as a brown 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 brown 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-e688501308e44fe9890b16ced0386b35
出典データセット
uspto-grants-2009_07
特許番号
US07566733B2

関連ノート

読み込み中…