Acetic Acid → N'-(3,5-difluoro-4-formylphenylsulfonyl)-N,N-dimethylformimidamide

HRID 1627383노트

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HRID 1627383 반응식
[F:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]=[CH:13][N:14]([CH3:16])[CH3:15])(=[O:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[Li+].CC([N-]C(C)C)C.CN([CH:28]=[O:29])C.CC(O)=O>C1COCC1.C(NC(C)C)(C)C.[Li]CCCC.O>[F:8][C:6]1[CH:5]=[C:4]([S:9]([N:12]=[CH:13][N:14]([CH3:16])[CH3:15])(=[O:10])=[O:11])[CH:3]=[C:2]([F:1])[C:7]=1[CH:28]=[O:29]

참가 물질

9

반응물 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 2724682Lithium diisopropylamideHCID 66740661N'-(3,5-difluorophenylsulfonyl)-N,N-dimethylformimidamide

생성물 1

HCID 86662257N'-(3,5-difluoro-4-formylphenylsulfonyl)-N,N-dimethylformimidamide수율 79.7%

시약·촉매·용매 4

HCID 7912Diisopropylamine촉매HCID 178418339Butyllithium촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

To a solution of diisopropylamine (231 mL, 1.63 mmol, 2.1 eq) in THF (1 L) was slowly added BuLi (2.5M in Hex, 653 mL, 1.63 mmol, 2.1 eq) at 0° C. The solution was cooled to −78° C., and then a solution of N′-(3,5-difluorophenylsulfonyl)-N,N-dimethylformimidamide (193 g, 777 mmol) in THF (1 L) was added dropwise to the stirred LDA solution over 1 h at −78° C. and allowed to stir another 2 h at same temperature. To the reaction mixture was added anhyd DMF (72 mL, 932 mmol, 1.2 eq) and, 30 minutes later, was added AcOH (50 mL) and water. The reaction mixture was extracted with EtOAc (500 mL×3). The combined extracts were washed with brine (1 L), dried over MgSO4 and concentrated in vacuo to give N′-(3,5-difluoro-4-formylphenylsulfonyl)-N,N-dimethylformimidamide (171 g), which was used in the next step without further purification.

후처리

  1. customat 0° C
  2. extractionThe reaction mixture was extracted with EtOAc (500 mL×3)
  3. washThe combined extracts were washed with brine (1 L)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-84346d24da954764b26d0e688f43621a
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785488B2

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