Pyridine → 3-(3-Methyl-1,2,4-thiadiazol-5-yl)-6-[[4-[3-(trifluoromethyl)phenoxy]butyl]thio]pyridazine

HRID 394490노트

반응식

HRID 394490 반응식
C[N:2](C)[C:3](=[N:5][C:6]([C:8]1[N:9]=[N:10][C:11]([S:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)=[CH:12][CH:13]=1)=[S:7])[CH3:4].N1C=CC=CC=1.NOS(O)(=O)=O>C(O)C.CO>[CH3:4][C:3]1[N:5]=[C:6]([C:8]2[N:9]=[N:10][C:11]([S:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)=[CH:12][CH:13]=2)[S:7][N:2]=1

참가 물질

6

반응물 3

HCID 1049PyridineHCID 76284hydroxylamine-O-sulfonic acidHCID 18176643HCID 18176643, 화합물

생성물 1

HCID 181766373-(3-Methyl-1,2,4-thiadiazol-5-yl)-6-[[4-[3-(trifluoromethyl)phenoxy]butyl]thio]pyridazine수율 26.1%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 887Methanol용매

실험 절차

A mixture of intermediate 13 (0.009 mol) and pyridine (0.02 mol) in ethanol (80 ml) was stirred. A mixture of hydroxylamine-O-sulfonic acid (0.01 mol) in methanol (20 ml) was added. The mixture was stirred overnight. The solvent was evaporated. The residue was taken up in DCM. The organic solution was washed with a diluted NaOH solution and with water, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent:DCM). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from 2-propanol. The precipitate was filtered off and dried, yielding 1 g (26%) of 3-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[[4-[3-(trifluoromethyl)phenoxy]butyl]thio]pyridazine (compound 94).

후처리

  1. additionwas added
  2. stirringThe mixture was stirred overnight
  3. customThe solvent was evaporated
  4. washThe organic solution was washed with a diluted NaOH solution and with water
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent:DCM)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. customThe residue was crystallized from 2-propanol
  12. filtrationThe precipitate was filtered off
  13. customdried

출처 및 근거

ORD 기록
ord-81ed27c031b245ae961b0eff76a714a9
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06602873B2

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