Dibutyltin oxide → 5-[4-[(5-nitro-thien-2-yl)ethynyl]-phenyl]-1H-tetrazole

HRID 1628

반응식

HRID 1628 반응식
[N+:1]([C:4]1[S:8][C:7]([C:9]#[C:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([Sn](=O)CCCC)CCC.C[Si]([N:33]=[N+:34]=[N-:35])(C)C>C1(C)C=CC=CC=1>[N+:1]([C:4]1[S:8][C:7]([C:9]#[C:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]3[NH:35][N:34]=[N:33][N:16]=3)=[CH:17][CH:18]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 196919534-[(5-Nitro-thien-2-yl)ethynyl]benzonitrile

생성물 1

HCID 1784183725-[4-[(5-nitro-thien-2-yl)ethynyl]-phenyl]-1H-tetrazole

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 4-[(5-nitro-2-thienyl)ethynyl]benzonitrile (0.6 g) and dibutyltin oxide (59 mg) in anhydrous toluene (30 ml) was added trimethylsilyl azide (0.5 ml). The reaction mixture was heated to reflux in the dark for 12 hours, then allowed to cool to room temperature. The reaction mixture was washed with saturated sodium bicarbonate (2×300 ml) and the combined aqueous layer was acidified to pH 1 with concentrated hydrochloric acid (30 ml). The acidified solution was washed with 1:1 ethyl acetate/tetrahydrofuran (500 ml) and the organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to dryness to give 5-[4-[(5-nitro-2-thienyl)ethynyl]-phenyl]-1H-tetrazole as a yellow solid.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux in the dark for 12 hours
  3. washThe reaction mixture was washed with saturated sodium bicarbonate (2×300 ml)
  4. washThe acidified solution was washed with 1:1 ethyl acetate/tetrahydrofuran (500 ml)
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness

출처 및 근거

ORD 기록
ord-ba45a428014e4c71895cdbed1fea1c2d
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726195

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