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Dimethylformamide → 3-(5-(Chloromethyl)-1,3,4-oxadiazol-2-yl)benzonitrile

HRID 732126
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HRID 732126 반응식
[Cl:1][CH2:2][C:3]([NH:5][NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[CH:9]=1)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[Cl:1][CH2:2][C:3]1[O:16][C:7]([C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=2)[C:14]#[N:15])=[N:6][N:5]=1
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참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 14812Phosphorus oxide (P4O10)HCID 54595588N'-(2-chloroacetyl)-3-cyanobenzohydrazide

생성물 1

HCID 201189383-(5-(Chloromethyl)-1,3,4-oxadiazol-2-yl)benzonitrile수율 29%

시약·촉매·용매 1

HCID 1140
Toluene
용매

실험 절차

N′-(chloroacetyl)-3-cyanobenzohydrazide (795 mg, 3.34 mmol) and P2O5 (4.7 g, 33.4 mmol) were added to DMF (6 ml) and toluene (4 ml). The reaction mixture was refluxed for 2 h. K2CO3 (aq., sat.) was added until pH was basic and the mixture was extracted with DCM. The combined organic layers were dried (Na2SO4) and purified with flash chromatography using 0 to 100% EA in hep. to give the title compound (209 mg, 29%). 1H NMR: 8.29 (m, 2 H), 7.82 (m, 1 H), 7.66 (t, 1 H), 4.78 (s, 2 H).

후처리

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. extractionthe mixture was extracted with DCM
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. custompurified with flash chromatography

출처 및 근거

ORD 기록
ord-33fd2f48fe344da6b7e6d9886e41e977
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07585881B2

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