Aniline → HCID 178488982、化合物

HRID 582143ノート

反応式

HRID 582143 の反応式
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3[NH:16][CH:17]=[C:18]([C:20](O)=[O:21])[N:19]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.O=S(Cl)Cl.[CH3:27][C:28]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[C:29]=1[NH2:30].NC1C=CC=CC=1.[H-].[Na+]>CN(C=O)C.C1COCC1.Cl>[CH3:27][C:28]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[C:29]=1[NH:30][C:20]([C:18]1[N:19]=[C:15]([C:9]2[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:8]=2)[NH:16][CH:17]=1)=[O:21]

参加物

9

反応物 5

HCID 6115AnilineHCID 68962,6-DimethylanilineHCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 178488985HCID 178488985、化合物

生成物 1

HCID 178488982HCID 178488982、化合物収率 15%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 313Hydrochloric Acid溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A mixture of 2-(3-cyclopentyloxy-4-methoxyphenyl)-imidazole-4-carboxylic acid (400 mg, 1.32 mmol) and SOCl2 (10 ml) containing DMF (1 drop) was heated to reflux for 2 hours. The volatiles were removed in vacuo and to the residue was added toluene (25 ml) and the solvent evaporated. This procedure was repeated to remove dissolved gaseous by-products. The residue was dissolved in THF (10 ml) and added dropwise at 0° C. over 10 minutes, to a solution of the salt of 2,6-dimethylaniline (510 μl, 4.14 mmol) in THF (30 ml) (formed by adding a solution of the aniline in THF (15 ml) to a suspension of NaH (167 mg, 4.14 mmol) is THF (15 ml) at room temperature). The resultant solution was stirred at room temperature for 48 hours, diluted with 1N HCl (20 ml) and the mixture extracted with methylene chloride (2×50 ml) The combined organics were dried over Na2SO4 and the volatiles removed in vacuo. Flash chromatography (SiO2 ; CH2Cl2 :EtOH (97:3)) afforded 2-(3-cyclopentyloxy-4-methoxyphenyl)-imidazole-4-carboxylic acid-2,6-dimethylphenyl amide (80 mg, 15%) as a pale yellow solid, mp 118-122° C.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. customThe volatiles were removed in vacuo and to the residue
  4. additionwas added toluene (25 ml)
  5. customthe solvent evaporated
  6. customto remove
  7. dissolutiondissolved gaseous by-products
  8. dissolutionThe residue was dissolved in THF (10 ml)
  9. customformed
  10. customat room temperature
  11. extractionthe mixture extracted with methylene chloride (2×50 ml) The combined
  12. dry with materialorganics were dried over Na2SO4
  13. customthe volatiles removed in vacuo

出典と根拠

ORDレコード
ord-68fc3a344c794634b79be972ab8e41ec
出典データセット
uspto-grants-1999_07
特許番号
US05922751

反応ノート

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