Dimethylamine → ethyl 4-(N,N-dimethylamidino)benzoate

HRID 878417노트

반응식

HRID 878417 반응식
[CH3:1][NH:2][CH3:3].[CH2:4]([Li])[CH2:5]CCCC.C(OC(=O)[C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1)C.[C:24](=[O:27])(O)[O-:25].[Na+]>O1CCCC1.CCCCCC>[CH2:4]([O:25][C:24](=[O:27])[C:15]1[CH:16]=[CH:17][C:18]([C:21](=[NH:22])[N:2]([CH3:3])[CH3:1])=[CH:19][CH:20]=1)[CH3:5]

참가 물질

7

반응물 4

HCID 674DimethylamineHCID 81589Ethyl 4-cyanobenzoateHCID 516892Sodium BicarbonateHCID 178506865HCID 178506865, 화합물

생성물 1

HCID 22631319ethyl 4-(N,N-dimethylamidino)benzoate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

To a tetrahydrofuran solution of 2M dimethylamine, 2.3M hexane solution of hexyllithium was slowly added over a period of at least three (3) hours while maintaining the temperature at between −8° C. and −12° C. This solution was added to the tetrahydrofuran solution of ethyl-4-cyanobenzoate (F) while maintaining the temperature between −8° C. and −12° C. The completion of the reaction was confirmed by HPLC, and the solution temperature was adjusted to between −8° C. and 3° C. The reaction mixture was slowly added to the cold solution of aqueous sodium bicarbonate solution and the desired ethyl-4-(N,N-dimethylcarbamimidoyl)benzoate (G) was extracted with ethyl acetate. The ethyl acetate layer was dried, filtered and evaporated under vacuum to afford ethyl-4-(N,N-dimethylcarbamimidoyl)benzoate (G) as a white solid.

후처리

  1. temperaturewhile maintaining the temperature at between −8° C. and −12° C
  2. temperaturewhile maintaining the temperature between −8° C. and −12° C
  3. customwas adjusted to between −8° C. and 3° C
  4. extractionthe desired ethyl-4-(N,N-dimethylcarbamimidoyl)benzoate (G) was extracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried
  6. filtrationfiltered
  7. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-6b8c5798f8b844fb8f5d4e50764ea7c2
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987463B2

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