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

HRID 1865163

反応式

HRID 1865163 の反応式
[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

参加物

4

反応物 3

HCID 1118Sulfuric AcidHCID 222194-BromobenzohydrazideHCID 31214Ethyl orthoformate

生成物 1

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

反応条件

温度
2.5 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-fee7d7fff28d4a59a7705338d0e3b656
出典データセット
uspto-grants-2009_12
特許番号
US07626020B2

関連ノート

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