Trifluoroacetic acid → HCID 10562764, compound

HRID 1987390Notes

Reaction equation

HRID 1987390 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[O:16])(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]1([CH3:17])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[CH2:15][OH:16])(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 189846511-[(4-Methylphenyl)sulfonyl]-1H-imidazole-2-carboxaldehyde

Product 1

HCID 10562764HCID 10562764, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the above aldehyde (1.53 g, 6.11 mmol) in CH2Cl2 (50 mL) at 0° C. was added TFA (5 mL) as described in J. Med. Chem. (1997) 40:2196. Purification by flash column chromatography using EtOAc/hexane (1:1) afforded [1-(toluene-4-sulfonyl)-1H-imidazol-2-yl]-methanol as a white solid (0.55 g, 36%). 1H NMR (CDCl3) δ 2.45 (s, 3H), 3.03 (br s, 1H), 4.84 (s, 2H), 6.99 (d, 1H, J=3.0 Hz), 7.35 (s, 1H), 7.39 (d, 2H, J=3.0 Hz), 7.83 (d, 2H, J=9.0 Hz).

Workup

  1. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-280294554dba40eb9fb7173b7eff54e8
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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