Dimethylformamide → 1-(5,6-Dichloro-benzimidazol-1-yl)-3,3-dimethyl-butan-2-ol

HRID 853834

반응식

HRID 853834 반응식
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]2[N:6]=[CH:7][NH:8][C:4]=2[CH:3]=1.[O:12]1[CH:14]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:13]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(OCC)(=O)C>[Cl:11][C:10]1[C:2]([Cl:1])=[CH:3][C:4]2[N:8]([CH2:13][CH:14]([OH:12])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH:7]=[N:6][C:5]=2[CH:9]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 921742-tert-ButyloxiraneHCID 3317755,6-Dichloro-1H-benzimidazole

생성물 1

HCID 589326341-(5,6-Dichloro-benzimidazol-1-yl)-3,3-dimethyl-butan-2-ol수율 73.3%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
160 °C

실험 절차

A large (2-5 mL) microwave reactor flask was charged with 5,6-dichlorobenzimidazole (571 mg, 3.1 mmol), 1,2-epoxy-3,3-dimethylbutane (307 mg, 3.1 mmol), powdered anhydrous potassium carbonate (424 mg, 3.1 mmol) and DMF (1.5 mL). The reaction was then heated in a microwave reactor for 6 minutes at 160° C. The reaction was then diluted with ethyl acetate and extracted with water three times. The organics were dried over MgSO4 and the solvent was removed. The residue was crystallized from CH2Cl2 to afford 653 mg (73%) of product as a white solid: 1H NMR (DMSO, 400 MHz) δ 1.06 (s, 9H), 3.47 (dd, 1H, J=2.0, J2=10.4), 4.08 (dd, 1H, J1=10.5, J2=14.4), 4.47 (dd, 1H, J1=2.0, J2=14.4), 7.75 (s, 1H), 7.79 (s, 1H), 8.23 (s, 1H); HPLC-MS calcd. for C21H22Cl2N4O2 (M+H+) 287.1, found 287.3.

후처리

  1. extractionextracted with water three times
  2. dry with materialThe organics were dried over MgSO4
  3. customthe solvent was removed
  4. customThe residue was crystallized from CH2Cl2

출처 및 근거

ORD 기록
ord-b0e6f8f091394914b5c91aaf2ba37a13
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07256207B2

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