Triethylamine → HCID 59331244, compound

HRID 1881813Notes

Reaction equation

HRID 1881813 reaction equation
[CH:1]1([CH2:6][CH:7]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)[C:8](=[O:11])[CH:9]=[CH2:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[S:22]1[CH:26]=[CH:25][N:24]=[C:23]1[CH:27]=[O:28].C(N(CC)CC)C>C(O)C.[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)(=O)C>[CH:1]1([CH2:6][CH:7]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)[C:8](=[O:11])[CH2:9][CH2:10][C:27]([C:23]2[S:22][CH:26]=[CH:25][N:24]=2)=[O:28])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27349031,3-Thiazole-2-carbaldehydeHCID 59331296HCID 59331296, compound

Product 1

HCID 59331244HCID 59331244, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution (5 mL) of 5-cyclopentyl-4-[4-(methylsulfonyl)phenyl]pent-1-en-3-one (790 mg) in ethanol were added 1,3-thiazole-2-carbaldehyde (275 μL), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (80 mg) and triethylamine (160 μL), and the mixture was stirred with heating under reflux for 8 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (850 mg, yield 79%) was obtained as colorless amorphous crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS: 420 (MH+).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 8 hr
  3. washwashed with water
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-70cc30bda9204687b82615e6685288a6
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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