Dimethyl Sulfoxide → HCID 59733153, compound

HRID 2276159Notes

Reaction equation

HRID 2276159 reaction equation
[CH:1]1([C:6]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=2[NH:15][C:16]([NH:18][C:19]2[S:20][CH:21]=[C:22]([CH2:24][OH:25])[N:23]=2)=[O:17])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(CC)CC.CS(C)=O.N1C=CC=CC=1.S(=O)(=O)=O>C(Cl)Cl.O>[CH:1]1([C:6]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=2[NH:15][C:16]([NH:18][C:19]2[S:20][CH:21]=[C:22]([CH:24]=[O:25])[N:23]=2)=[O:17])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 59733044HCID 59733044, compound

Product 1

HCID 59733153HCID 59733153, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To 1-(2-cyclopentanecarbonyl-4-methyl-phenyl)-3-[4-hydroxymethyl-thiazol-2-yl]-urea (1.8 g, 5 mmol) in CH2Cl2 (40 mL) at 0° C. was added Et3N (2.88 mL, 20 mmol), dimethyl sulfoxide (10 mL) followed by sulfur trioxide-pyridine (2.38 g, 15.0 mmol). The reaction mixture was stirred for 1 h and then poured into water (30 mL). The mixture was extracted with CH2Cl2 and the organic layers was washed with 1.0 N ammonium chloride (2×20 mL), water (2×20 mL), brine (1×20 mL), dried (Na2SO4) and concentrated to give a solid. The solid was purified by column chromatography (silica, Hexanes/EtOAc, 20-50%) to obtain 1-(2-cyclopentanecarbonyl-4-methyl-phenyl)-3-(4-formyl-thiazol-2-yl)-urea (1.59 g, 86%) as a white solid.

Workup

  1. extractionThe mixture was extracted with CH2Cl2
  2. washthe organic layers was washed with 1.0 N ammonium chloride (2×20 mL), water (2×20 mL), brine (1×20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto give a solid
  6. customThe solid was purified by column chromatography (silica, Hexanes/EtOAc, 20-50%)

Sources & evidence

ORD record
ord-30c0251ecd5342d1a5453ddadf8fbf7c
Source dataset
uspto-grants-2015_09
Patent number
USRE045670E1

Reaction notes

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