Sodium Sulfate → HCID 11951959, compound

HRID 2101506Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([Cl:23])[CH:22]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[NH:11][C:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.C(Cl)Cl.O>[CH2:12]([NH:11][C:7]1[N:6]([CH2:5][C:4]2[CH:20]=[C:21]([Cl:23])[CH:22]=[C:2]([Cl:1])[CH:3]=2)[CH:10]=[CH:9][N:8]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 70 °C

Procedure

N-[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-yl]-benzamide, was dissolved in anhydrous THF and 1M LiAlH4 was added to the reaction solution at room temperature. The reaction mixture was then heated to 70° C. and stirred for 10 min. The mixture was then diluted with CH2Cl2 and water was slowly added until H2 formation stopped. The reaction mixture was passed through a cartridge packed with anhydrous Na2SO4. The filtrated was concentrated and purified by silica gel preparative TLC using 95:5 CH2Cl2:MeOH to afford the title compound (5 mg, 7%); MS m/z 332 [C17H15Cl2N3+H]+.

Workup

additionwas slowly added until H2 formation
concentrationThe filtrated was concentrated
custompurified by silica gel preparative TLC

Sources & evidence

ORD record: ord-977fb181cd2d484084bf129d84f8b60a
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572921B2

Reaction notes

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