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

HRID 853834

Reaction equation

HRID 853834 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b0e6f8f091394914b5c91aaf2ba37a13
Source dataset
uspto-grants-2007_08
Patent number
US07256207B2

Linked notes

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