Sulfuric Acid → 2-(4-Bromophenyl)-1,3,4-oxadiazole

HRID 1865163

반응식

HRID 1865163 반응식
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:17](OC(OCC)OCC)C>>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[O:7][CH:17]=[N:9][N:8]=2)=[CH:4][CH:3]=1

참가 물질

4

반응물 3

HCID 1118Sulfuric AcidHCID 222194-BromobenzohydrazideHCID 31214Ethyl orthoformate

생성물 1

HCID 7151202-(4-Bromophenyl)-1,3,4-oxadiazole수율 89.9%

반응 조건

온도
2.5 °C

실험 절차

To a suspension of 4-bromobenzoic hydrazide (200 g) in industrial methylated spirit (700 ml) was added triethylorthoformate (309 ml), industrial methylated spirit (100 ml) and sulphuric acid (0.8 ml). The reaction mixture was heated to reflux for 1 hour. The reaction mixture was cooled to 0-5° C. and product crystallised. Product was isolated, washed and dried to yield 2-(4-bromophenyl)-1,3,4-oxadiazole (186.1 g, 89.9%). 400 MHz NMR Spectrum: (DMSOd6) 9.35 (s, 1H), 7.98 (d, 1H), 7.95 (d, 1H), 7.84 (d, 1H), 7.81 (d, 1H); Mass Spectrum MH+ 224.9663 (calc. using 79-Br) Found 224.9701.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. customproduct crystallised
  4. customProduct was isolated
  5. washwashed
  6. customdried

출처 및 근거

ORD 기록
ord-fee7d7fff28d4a59a7705338d0e3b656
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07626020B2

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