4-Methoxy-2,2,6,6-tetramethylpiperidinyl-1-oxy → 1-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone

HRID 230451

反応式

HRID 230451 の反応式
[Cl:1][C:2]1[C:16]([Cl:17])=[CH:15][C:5]2[NH:6][C:7]([CH:9]([OH:14])[C:10]([F:13])([F:12])[F:11])=[N:8][C:4]=2[CH:3]=1.CC1(C)N([O-])C(C)(C)CC(OC)C1.[Br-].[K+].Cl[O-].[Na+]>C1COCC1.O.C(OCC)(=O)C>[Cl:17][C:16]1[C:2]([Cl:1])=[CH:3][C:4]2[NH:8][C:7]([C:9](=[O:14])[C:10]([F:13])([F:11])[F:12])=[N:6][C:5]=2[CH:15]=1

参加物

8

反応物 4

HCID 1253234-Methoxy-2,2,6,6-tetramethylpiperidinyl-1-oxyHCID 253877Potassium BromideHCID 116377781-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanolHCID 23665760Sodium Hypochlorite

生成物 1

HCID 115943701-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1-(5,6-Dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanol (0.29 g; 1.00 mmole), 4-methoxy-2,2,6,6-tetramethyl-1-piperdinyloxy free radical (4-methoxy-TEMPO free radical; 4.4 mg; 0.03 mmoles) and potassium bromide (KBr; 13 mg; 0.11 mmoles) were dissolved in THF (2.9 mL). The reaction mixture was stirred while cooled to −10° C., after 10 min. a sodium hypochlorite solution (bleach; 10-13% aqueous; 2.10 mL; 3.53 mmoles) was added and allowed to stir for 15 min., then warmed to room temperature and stirred for 15 min. The reaction mixture was diluted with water (20 mL) and ethyl acetate (30 mL), the layers were separated and the aqueous layer was extracted with ethyl acetate (3×30 mL). The extracts were combined and washed with water (30 mL) and brine (40 mL), then dried over Na2SO4. The filtrate was concentrated in vacuo and purified by column chromatography (SiO2; 100% ether) to yield the title compound as a light yellow solid.

後処理

  1. additionwas added
  2. stirringto stir for 15 min.
  3. stirringstirred for 15 min
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted 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. custompurified by column chromatography (SiO2; 100% ether)

出典と根拠

ORDレコード
ord-5ad2aee07fae4b059fa528ab3e820a87
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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