Dimethylformamide → 7-Thia-2,4,5-triazatricyclo(6.4.0.0,2,6)dodeca-1(12),3,5,8,10-pentaene

HRID 1578527노트

반응식

HRID 1578527 반응식
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]=[S:10].CN(C=O)C.[CH:16]([NH:18][NH2:19])=O.[H-].[Na+]>O>[N:19]1[N:18]=[CH:16][N:8]2[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[S:10][C:9]=12

참가 물질

6

반응물 4

HCID 6228Dimethylformamide2회HCID 12229HydrazinecarboxaldehydeHCID 24758Sodium hydrideHCID 1231711-Chloro-2-isothiocyanatobenzene

생성물 1

HCID 2545687-Thia-2,4,5-triazatricyclo(6.4.0.0,2,6)dodeca-1(12),3,5,8,10-pentaene

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
160 °C

실험 절차

Five grams (30.0 mmoles) of o-chlorophenylisothiocyanate were dissolved in 50 ml. of dry DMF. A solution of 1.8 g. (30.0 mmoles) of formylhydrazine in 50 ml. of dry DMF was added dropwise rapidly to the stirred reaction mixture. The temperature of the reaction rose to about 45°C. The temperature was maintained between 60°C. and 100°C. for 24 hours. Thirty millimoles, 1.5 g., of sodium hydride as a 50% mineral oil suspension was added to the reaction mixture. The reaction was completed by heating at reflux temperature (160°C.) for about 185 hours. The cooled mixture was poured into water. The aqueous mixture was extracted with n-hexane to remove mineral oil. The product was extracted with ethyl acetate. The ethyl acetate extract was washed (water), dried (MgSO4) and evaporated in vacuo to a residual oil. The oil was covered with dry ether and the product crystallized upon standing. The yield of s-triazolo[3,4-b]benzothiazole, m.p. about 175°-176°C., was 200 mg.

후처리

  1. customrose to about 45°C
  2. temperatureThe temperature was maintained between 60°C. and 100°C. for 24 hours
  3. temperatureby heating
  4. extractionThe aqueous mixture was extracted with n-hexane
  5. customto remove mineral oil
  6. extractionThe product was extracted with ethyl acetate
  7. extractionThe ethyl acetate extract
  8. washwas washed (water)
  9. dry with materialdried (MgSO4)
  10. customevaporated in vacuo to a residual oil
  11. customthe product crystallized

출처 및 근거

ORD 기록
ord-0b6cb98a04344d3fbc604b14d70c5287
출처 데이터셋
uspto-grants-1976_02
특허 번호
US03937713

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