Cyanogen Bromide → 5-(Naphthalen-2-yl)-1,3,4-oxadiazol-2-amine

HRID 619333

반응식

HRID 619333 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:13][NH2:14])=[O:12].C(=O)([O-])O.[Na+].[N:20]#[C:21]Br>O1CCOCC1.O.C(O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[O:12][C:21]([NH2:20])=[N:14][N:13]=1

참가 물질

7

반응물 3

HCID 10476Cyanogen BromideHCID 1234852-NaphthohydrazideHCID 516892Sodium Bicarbonate

생성물 1

HCID 187074765-(Naphthalen-2-yl)-1,3,4-oxadiazol-2-amine수율 20%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

To a stirred solution of naphthalene-2-carboxylic acid hydrazide (0.6 g, 3.22 mmol, prepared as described in example 1) in dioxane (20 ml) was added a solution of sodium hydrogen carbonate (0.27 g, 3.22 mmol) in water (15 ml) and the resulting mixture was stirred for 5 min. To the reaction mixture was added cyanogen bromide (0.35 g, 3.3 mmol) and the mixture was stirred for 3 h at room temperature. The precipitate was filtered off and washed with diethyl ether (2×15 ml) and dried in vacuo at 50° C. affording 0.4 g of crude product which was suspended in absolute ethanol (15 ml) and stirred at reflux temperature for 0.5 h. The cooled suspension was filtered and the filter cake was dried in vacuo at 50° C. affording 130 mg (20%) of the title compound as a solid.

후처리

  1. stirringthe mixture was stirred for 3 h at room temperature
  2. filtrationThe precipitate was filtered off
  3. washwashed with diethyl ether (2×15 ml)
  4. customdried in vacuo at 50° C.
  5. customaffording 0.4 g of crude product which
  6. stirringstirred
  7. temperatureat reflux temperature for 0.5 h
  8. filtrationThe cooled suspension was filtered
  9. customthe filter cake was dried in vacuo at 50° C.

출처 및 근거

ORD 기록
ord-74ce89f4603944c88def162dc4d10b8f
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05958957

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