Dimethylformamide → N,N,N',N'-Tetramethylazodicarboxamide

HRID 254815

반응식

HRID 254815 반응식
C(Cl)(=O)C(Cl)=O.[CH3:7][N:8]([CH:10]=[O:11])[CH3:9].[C:12]([NH:18][NH2:19])(=[O:17])C(C)(C)C.[CH2:20]([N:22](CC)[CH2:23]C)C>C(Cl)Cl>[CH3:7][N:8]([C:10]([N:19]=[N:18][C:12]([N:22]([CH3:23])[CH3:20])=[O:17])=[O:11])[CH3:9]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 5451472,2-Dimethylpropanehydrazide

생성물 1

HCID 4278N,N,N',N'-Tetramethylazodicarboxamide수율 61%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To the solution of acid (63) (330 mg, 0.74 mmol) in CH2Cl2 (10 mL) was added oxalyl chloride (77 μL, 0.88 mmol) and the catalytic amount of DMF. The reaction mixture was stirred for 1 hr and concentrated in vacuo. The residue (crude acyl chloride) was diluted with CH2Cl2 (10 mL) and pivalohydrazide (128 mg, 1.10 mmol) and triethylamine (0.31 mL, 2.21 mmol) was added. The reaction mixture was stirred for 2 hrs at room temperature. The reaction mixture was concentrated in vacuo and diluted with EtOAc (50 mL). The organic layer was washed with aq. 1N HCl and aq. sat'd NaHCO3 solution, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. Purification by Prep-LC (Gilson) provided 244 mg (61%) of desired diamide as solid.

후처리

  1. concentrationconcentrated in vacuo
  2. additionwas added
  3. stirringThe reaction mixture was stirred for 2 hrs at room temperature
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. additiondiluted with EtOAc (50 mL)
  6. washThe organic layer was washed with aq. 1N HCl and aq. sat'd NaHCO3 solution
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by Prep-LC (Gilson)

출처 및 근거

ORD 기록
ord-55edbabeaad54a1ab3564d665f61bf4d
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875647B2

연결된 노트

불러오는 중…