Triethylamine → HCID 57558451, compound

HRID 2382532Notes

Reaction equation

HRID 2382532 reaction equation
[C:1]([C:5]1[CH:25]=[CH:24][C:8]([CH2:9][S:10][C:11]2[O:12][C:13]3[C:18]([C:19](=[O:23])[C:20]=2[CH2:21][OH:22])=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:26]1(C)[C:27]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:29]=[CH:30][CH:31]=1.[CH2:37](N(CC)CC)C>ClCCl>[C:1]([C:5]1[CH:25]=[CH:24][C:8]([CH2:9][S:10][C:11]2[O:12][C:13]3[C:18]([C:19](=[O:23])[C:20]=2[CH2:21][O:22][S:32]([C:27]2[CH:26]=[CH:31][C:30]([CH3:37])=[CH:29][CH:28]=2)(=[O:33])=[O:34])=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 57558470HCID 57558470, compound

Product 1

HCID 57558451HCID 57558451, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 25 mL round bottom flask is introduced 2-(4-tert-butylbenzyl)thio-3-hydroxymethyl chromen-4-one (3 g, 8.47 mmol) and this is dissolved in dichloromethane (10 mL). Toluenesulfonyl chloride (12.7 mmol) and triethylamine (12.7 mmol) are then added to it and the reaction mixture is stirred for 4 hours at room temperature. The solvent is then removed in vacuo and the residue obtained is purified by silica gel flash chromatography (ethyl acetate:hexanes) to get the above-mentioned compound.

Workup

  1. customThe solvent is then removed in vacuo
  2. customthe residue obtained
  3. customis purified by silica gel flash chromatography (ethyl acetate:hexanes)
  4. customto get the above-mentioned compound

Sources & evidence

ORD record
ord-b8ddae5998af4aa09707be32e880b7ff
Source dataset
uspto-grants-2012_09
Patent number
US08263042B2

Reaction notes

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