Benzaldehyde → N-benzyl-5-methyl-1,3,4-thiadiazol-2-amine

HRID 236895노트

반응식

HRID 236895 반응식
[NH2:1][C:2]1[S:3][C:4]([CH3:7])=[N:5][N:6]=1.[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[BH4-].[Na+]>C(O)C>[CH3:7][C:4]1[S:3][C:2]([NH:1][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][N:5]=1

참가 물질

5

반응물 3

HCID 240BenzaldehydeHCID 669491,3,4-Thiadiazole, 2-amino-5-methyl-HCID 4311764Sodium borohydride2회

생성물 1

HCID 6460923N-benzyl-5-methyl-1,3,4-thiadiazol-2-amine수율 75.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

2-Amino-5-methyl-1,3,4-thiadiazole (23 g, 0.2 mole) and benzaldehyde (29.6 ml, 0.3 mole) were refluxed together in ethanol (200 ml) for 11/2 hours. The solution was cooled to room temperature and sodium borohydride (11.35 g, 0.3 mole) added over 5 to 10 minutes. The mixture was refluxed for 4 hours, treated with further sodium borohydride (5 g) and refluxed overnight. The ethanol was evaporated off, the residue treated with water and extracted with ether. The ether extract was dried over sodium sulphate, filtered and evaporated to leave an oil which solidified. This solid was triturated with ether, filtered, washed with light petroleum (b.p. 40°-60° C.) and again triturated with ether and filtered to give N-(5-methyl-1,3,4-thiadiazol-2-yl)-benzylamine (30.95 g), which on recrystallisation from ether had m.p. 140° C.

후처리

  1. temperatureThe mixture was refluxed for 4 hours
  2. temperaturerefluxed overnight
  3. customThe ethanol was evaporated off
  4. additionthe residue treated with water
  5. extractionextracted with ether
  6. extractionThe ether extract
  7. dry with materialwas dried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated
  10. customto leave an oil which
  11. customThis solid was triturated with ether
  12. filtrationfiltered
  13. washwashed with light petroleum (b.p. 40°-60° C.)
  14. customagain triturated with ether
  15. filtrationfiltered

출처 및 근거

ORD 기록
ord-210fbb6c76274aa48c907f4f97d0d15f
출처 데이터셋
uspto-grants-1979_06
특허 번호
US04158659

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