Triethylamine → HCID 59331400, compound

HRID 1881928Notes

Reaction equation

HRID 1881928 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH2:16][CH:17]2[CH2:21][CH2:20][O:19][CH2:18]2)[C:12](=[O:15])[CH:13]=[CH2:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[N:22]1[CH:27]=[CH:26][N:25]=[CH:24][C:23]=1[CH:28]=[O:29].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>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH2:16][CH:17]2[CH2:21][CH2:20][O:19][CH2:18]2)[C:12](=[O:15])[CH2:13][CH2:14][C:28]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][N:22]=2)=[O:29])=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 11274980Pyrazine-2-carbaldehydeHCID 59331472HCID 59331472, compound

Product 1

HCID 59331400HCID 59331400, compoundYield 14.2%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 4-[4-(methylsulfonyl)phenyl]-5-(tetrahydrofuran-3-yl)pent-1-en-3-one (523 mg) in ethanol (8.5 mL) were added pyrazine-2-carbaldehyde (220 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (50.5 mg) and triethylamine (102 μL), and the mixture was stirred with heating under reflux for 3 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (100 mg, yield 14%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (19:1, volume ratio).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 3 hr
  3. washwashed with water
  4. dry with materialThe ethyl acetate layer was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4105138dc1ff4a54ad7e8479cf64f9ea
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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