Toluene → HCID 178441684、化合物

HRID 375457ノート

反応式

HRID 375457 の反応式
[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]#[N:27])=[CH:16][CH:15]=2)[C:7]([CH2:11][OH:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].C([Sn]([N:53]=[N+:54]=[N-:55])(CCCCCCCC)CCCCCCCC)CCCCCCC.C1(C)C=CC=CC=1>CN(C)C=O>[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[NH:55][N:54]=[N:53][N:27]=3)=[CH:18][CH:19]=2)[C:7]([CH2:11][OH:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

参加物

5

反応物 3

HCID 1140TolueneHCID 144256644'-((2-Butyl-4-chloro-5-(hydroxymethyl)-1H-imidazol-1-yl)methyl)(1,1'-biphenyl)-2-carbonitrileHCID 71354122Azido(trioctyl)stannane

生成物 1

HCID 178441684HCID 178441684、化合物収率 94.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
115 °C

実験手順

A mixture of 5 g of 2-butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)methyl]-5-(hydroxymethyl)imidazole, 30.2 g of trioctyltin azide (tri-n-octyltin azide), 25 ml of toluene and 1 ml of dimethylformamide was stirred for 24 hours at 115° C. in nitrogen streams. The reaction mixture was, after cooling, concentrated, and there were added 40 ml of ethanol and a solution of 5.2 g of sodium nitrite in 19 ml of water, whose pH was adjusted at 3.4 with conc. hydrochloric acid. The resultant mixture was subjected to extraction with methylene chloride, and the extract was concentrated under reduced pressure. To the concentrate was added hexane, then resulting crystalline precipitates were collected by filtration. The crystals were washed with hexane, then dried to afford 5.27 g (yield 94.7%) of 2-butyl-4-chloro-5-(hydroxymethyl)-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]imidazole. The NMR spectrum of the product was in good agreement with that described in J. Med. Chem., 1991, 34, 2525.

後処理

  1. temperatureafter cooling
  2. concentrationconcentrated
  3. additionthere were added 40 ml of ethanol
  4. extractionThe resultant mixture was subjected to extraction with methylene chloride
  5. concentrationthe extract was concentrated under reduced pressure
  6. additionTo the concentrate was added hexane
  7. customresulting crystalline precipitates
  8. filtrationwere collected by filtration
  9. washThe crystals were washed with hexane
  10. customdried

出典と根拠

ORDレコード
ord-9dc48f35294e4532a2a7e2fb1e0a95a3
出典データセット
uspto-grants-1996_01
特許番号
US05484955

反応ノート

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