Sodium hydride → 3-(5-(Methylthio)-1,3,4-thiadiazol-2-ylthio)pyrazine-2-carbonitrile

HRID 1968389노트

반응식

HRID 1968389 반응식
[CH3:1][S:2][C:3]1[S:7][C:6]([SH:8])=[N:5][N:4]=1.[H-].[Na+].Cl[C:12]1[C:13]([C:18]#[N:19])=[N:14][CH:15]=[CH:16][N:17]=1>CN(C=O)C.C1C=CC=CC=1>[CH3:1][S:2][C:3]1[S:7][C:6]([S:8][C:12]2[C:13]([C:18]#[N:19])=[N:14][CH:15]=[CH:16][N:17]=2)=[N:5][N:4]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 2924653-Chloropyrazine-2-carbonitrileHCID 1785036205-methylsulfanyl-1,3,4-thiadiazole-2-thiol

생성물 1

HCID 28214693-(5-(Methylthio)-1,3,4-thiadiazol-2-ylthio)pyrazine-2-carbonitrile

시약·촉매·용매 2

HCID 241Benzene용매HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To a solution of 5-(methylthio)-1,3,4-thiadiazole-2-thiol (821 mg, 5.0 mmol) in DMF and benzene (10 ml, 1/1) was added NaH (60% dispersion in mineral oil, 220 mg, 5.5 mmol) slowly at 0° C. under nitrogen atmosphere. The resulting suspension was stirred at 0° C. for 15 minutes and then to the mixture was added 3-chloropyrazine-2-carbonitrile (698 mg, 5.0 mmol). The reaction was stirred at 80° C. for 4 hr. The reaction was then cooled to room temperature and quenched with saturated NH4Cl solution and extracted with EtOAc. The combined organic layers were washed with water, brine and dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography on silica gel to give the title compound as a white solid.

후처리

  1. stirringThe reaction was stirred at 80° C. for 4 hr
  2. temperatureThe reaction was then cooled to room temperature
  3. customquenched with saturated NH4Cl solution
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-92e6f8105c1f43dbab2d3d74c05faeca
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426358B2

반응 노트

불러오는 중…