Pyrazole → 1-(N-cyano-N'-methylamidino)pyrazole

HRID 1702477노트

반응식

HRID 1702477 반응식
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[N:4]1.[C:8]([NH:10][C:11](S(C)=O)=[N:12][CH3:13])#[N:9]>C1COCC1>[C:8]([NH:10][C:11]([N:3]1[CH:7]=[CH:6][CH:5]=[N:4]1)=[N:12][CH3:13])#[N:9]

참가 물질

5

반응물 3

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 12918611N-cyano-N'-methyl-methylsulfinylformamidine

생성물 1

HCID 129186121-(N-cyano-N'-methylamidino)pyrazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred suspension of NaH (50% oil suspension, 3.58 g) in THF (160 ml) was added pyrazole (5.84 g) at a temperature below room temperature and stirred for 1 hr. To the mixture was added N-cyano-N'-methyl-methylsulfinylformamidine (8.32 g, obtained by the same procedure as in Example 3 (1)) and stirred for 3 hrs. at room temperature. After evaporation under a reduced pressure, the residue was dissolved in water and washed with ether. The aqueous layer was acidified (pH 4) with 10% HCl under ice-cooling. The precipitate was filtered, washed with water and dried to give 1-(N-cyano-N'-methylamidino)pyrazole (7.52 g). An additional amount (0.2 g) of the same product was further obtained from the filtrate. The crude products were combined and recrystallized from ethyl acetate to give the purified product (6.12 g). Yield 71.7%, m.p. 166.5°-168° C.

후처리

  1. stirringstirred for 3 hrs
  2. customat room temperature
  3. customAfter evaporation under a reduced pressure
  4. dissolutionthe residue was dissolved in water
  5. washwashed with ether
  6. temperaturecooling
  7. filtrationThe precipitate was filtered
  8. washwashed with water
  9. customdried

출처 및 근거

ORD 기록
ord-4e7ad4ae91964ac9acf46f8750be129e
출처 데이터셋
uspto-grants-1983_04
특허 번호
US04381395

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