Thionyl Chloride → N-(3-(1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-iodo-4-methylbenzamide

HRID 572961ノート

反応式

HRID 572961 の反応式
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.S(Cl)(Cl)=O.[N:16]1([C:21]2[CH:22]=[C:23]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=2)[NH2:24])[CH:20]=[CH:19][N:18]=[CH:17]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[N:16]1([C:21]2[CH:22]=[C:23]([NH:24][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][C:10]([CH3:11])=[C:2]([I:1])[CH:3]=3)[CH:25]=[C:26]([C:28]([F:30])([F:31])[F:29])[CH:27]=2)[CH:20]=[CH:19][N:18]=[CH:17]1

参加物

6

反応物 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 6216403-Iodo-4-methylbenzoic acidHCID 442226373-(1H-Imidazol-1-YL)-5-(trifluoromethyl)aniline

生成物 1

HCID 44222638N-(3-(1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-iodo-4-methylbenzamide収率 84.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To 3-Iodo-4-methylbenzoic acid (3.07 g, 0.0117 mol) was added thionyl chloride (10 mL) and refluxed for 2 h. The excess thionyl chloride was carefully removed and the resulting acid chloride was dried in vacuo for 2 h. The residue was then dissolved in DCM (anhydrous, 25 mL) and cooled on ice. To the cooled solution was added 3-(1H-imidazol-1-yl)-5-(trifluoromethyl)aniline 5 (3.46 g, 0.0152 mol) in DCM followed by the dropwise addition of diisopropylethylamine (8.2 mL, 0.047 mol). This was stirred at ambient temperature for 21 h. The white solid that separated was filtered and washed with water and dried to provide 4.65 g of product. Additional product could be obtained from the filtrate following concentration and purification by silica gel flash chromatography in EtOAc/hexanes.

後処理

  1. temperaturerefluxed for 2 h
  2. customThe excess thionyl chloride was carefully removed
  3. dry with materialthe resulting acid chloride was dried in vacuo for 2 h
  4. dissolutionThe residue was then dissolved in DCM (anhydrous, 25 mL)
  5. temperaturecooled on ice
  6. customThe white solid that separated
  7. filtrationwas filtered
  8. washwashed with water
  9. customdried

出典と根拠

ORDレコード
ord-5aa11fe4421a4a4b98a9f6488256ea13
出典データセット
uspto-grants-2015_05
特許番号
US09029533B2

反応ノート

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