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Triphenylcarbinol → 2-(1-Trityl-1H-imidazol-4-yl)-benzonitrile

HRID 1795257
ノート
印刷プレビュー

反応式

HRID 1795257 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[CH:10][N:11]([C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=1.[Cu][C:33]#[N:34].C(O)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>CN(C)C=O.C1(C)C=CC=CC=1>[C:13]([N:11]1[CH:12]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[C:33]#[N:34])[N:9]=[CH:10]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6457TriphenylcarbinolHCID 221851434-(2-bromophenyl)-1-trityl-1H-imidazoleHCID 178418546HCID 178418546、化合物

生成物 1

HCID 221851592-(1-Trityl-1H-imidazol-4-yl)-benzonitrile

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 4-(2-bromo-phenyl)-1-trityl-1H-imidazole (73.0 g, 163.3 mmol) in dimethylformamide (500 ml) was added copper (I) cyanide (17.5 g, 195.9 mmol). The reaction was heated to ˜80° C. under nitrogen for 14 h. After cooling to about 50° C., the reaction was diluted with toluene (ca. 300 ml) and slowly poured onto ammonium hydroxide (3N, 1.5 L) while stirring vigorously. The mixture was stirred for 40 min and then filtered in vacuo over a bed of celite (slow filtration, required ˜2 h). The phases were separated and the organic layer was washed with brine (75 ml×3) and dried (sodium sulfate). Concentration of the solvent afforded a light brown solid. The crude product contains ˜10–15% of trityl alcohol (by HPLC) and was used without further purification in the subsequent step.

後処理

  1. temperatureAfter cooling to about 50° C.
  2. additionslowly poured onto ammonium hydroxide (3N, 1.5 L)
  3. stirringThe mixture was stirred for 40 min
  4. filtrationfiltered in vacuo over a bed of celite (
  5. filtrationslow filtration
  6. custom˜2 h
  7. customThe phases were separated
  8. washthe organic layer was washed with brine (75 ml×3)
  9. dry with materialdried (sodium sulfate)
  10. customConcentration of the solvent afforded a light brown solid
  11. customwas used without further purification in the subsequent step

出典と根拠

ORDレコード
ord-6268f68576ce443bb9613929eb45e039
出典データセット
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07026324B2

反応ノート

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