Toluene → HCID 178441684, 화합물

HRID 375457노트

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HRID 375457 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 178441684HCID 178441684, 화합물수율 94.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
115 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9dc48f35294e4532a2a7e2fb1e0a95a3
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05484955

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