Dimethyl Sulfoxide → HCID 59239988, compound

HRID 1673053Notes

Reaction equation

HRID 1673053 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:13]=[C:14]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([S:38]([CH3:41])(=[O:40])=[O:39])[CH:33]=2)[CH:15]=[CH:16][C:17]=1[N:18]1[CH:22]=[C:21]([CH2:23][OH:24])[N:20]=[C:19]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[Cl:11][C:12]1[CH:13]=[C:14]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([S:38]([CH3:41])(=[O:40])=[O:39])[CH:33]=2)[CH:15]=[CH:16][C:17]=1[N:18]1[CH:22]=[C:21]([CH:23]=[O:24])[N:20]=[C:19]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59240150HCID 59240150, compound

Product 1

HCID 59239988HCID 59239988, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a −78° C. solution of oxalyl chloride (0.20 mL, 2.33 mmol) in 5 mL dichloromethane was added DMSO dropwise followed by (1-(3-chloro-3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-chlorophenyl)-1H-imidazol-4-yl)methanol (735 mg, 1.55 mmol) in 5 mL of dichloromethane. Triethylamine (1.3 mL, 9.30 mmol) was then added at −78° C. and the reaction was stirred 12 h and warmed to room temperature. The reaction was diluted with 50 mL ethyl acetate, washed with water 1×50 mL, brine, and dried with MgSO4. The solvent was removed in vacuo and the residue was purified by column chromatography using hexanes:ethyl acetate as eluents to afford 1-(3-chloro-3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-chlorophenyl)-1H-imidazole-4-carbaldehyde (338 mgs, 47%) as a white solid. 1H-NMR (DMSO, 400 MHz) δ 9.90 (s, 1H), 8.56 (s, 1H), 8.22-8.21 (m, 1H), 8.12-8.09 (m, 2H), 7.97-7.94 (m, 1H), 7.84 (dd, J=8.33 Hz, J=2.04 Hz, 1H), 7.75 (t, J=7.82 Hz, 1H), 7.67-7.65 (m, 1H), 7.58-7.56 (m, 1H), 7.50-7.43 (m, 2H), 7.40-7.36 (m, 1H), 3.30 (s, 3H); MS (ES) 471.0 [M+H]+.

Workup

  1. washwashed with water 1×50 mL, brine
  2. dry with materialdried with MgSO4
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5e166714526645e482d152722c28d71f
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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