Dimethyl Sulfoxide → HCID 59749538, compound

HRID 747277Notes

Reaction equation

HRID 747277 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][C:13]1[CH:37]=[CH:36][C:16]([CH2:17][S:18][C:19]2[NH:23][CH:22]([CH:24]([C:26]3[CH:35]=[CH:34][CH:33]=[C:32]4[C:27]=3[CH:28]=[CH:29][CH:30]=[N:31]4)[CH3:25])[CH2:21][N:20]=2)=[CH:15][CH:14]=1.C(N(CC)CC)C>C(Cl)Cl.[Cl-].[Na+].O>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][S:18][C:19]2[NH:23][C:22]([CH:24]([C:26]3[CH:35]=[CH:34][CH:33]=[C:32]4[C:27]=3[CH:28]=[CH:29][CH:30]=[N:31]4)[CH3:25])=[CH:21][N:20]=2)=[CH:36][CH:37]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59749535HCID 59749535, compound2×

Product 1

HCID 59749538HCID 59749538, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent5×HCID 57417360Sodium chloride; waterSolvent

Procedure

A Swern-type reagent was formed in standard fashion: oxalyl chloride (9.15 mL as a 2M soln. in CH2Cl2) in CH2Cl2 (23 mL) was cooled to −78° C. and treated with a solution of DMSO (2.85 mL, 36.8 mmol) in CH2Cl2 (23 mL) for 30 m. To this solution was added 5-{-1[2-(4-methoxy-benzylsulfanyl)-4,5-dihydro-3H-imidazol-4-yl]-ethyl}-quinoline (Intermediate E5) (4.7 g, 12.4 mmol) in CH2Cl2 (30 mL) and stirring continued for 45 m at −78° C. Triethylamine (9 mL) was added at −78° C. and warmed to rt for 40 m. The reaction mixture was diluted with brine and CH2Cl2. The aqueous layer was extracted with ethyl acetate. The organic solution was dried over MgSO4, filtered and evaporated to dryness. Chromatography on SiO2 with 80 to 100% ethyl acetate:hexanes yielded 5-{1-[2-(4-methoxy-benzylsulfanyl)-3H-imidazol-4-yl]-ethyl}-quinoline (Intermediate E6) 3.45 g (74%).

Workup

  1. customA Swern-type reagent was formed in standard fashion
  2. customcontinued for 45 m at −78° C
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-dd489c62a0f94ed1a5b213c78e5c4baf
Source dataset
uspto-grants-2008_07
Patent number
US07396849B2

Reaction notes

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