Triethylamine → HCID 57431972, compound

HRID 860642Notes

Reaction equation

HRID 860642 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1.[CH3:13][N:14]([CH3:18])[C:15](Cl)=[S:16].C(N(CC)CC)C>O1CCOCC1>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:15](=[S:16])[N:14]([CH3:18])[CH3:13])[CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27871Dimethylthiocarbamoyl chlorideHCID 39129Methyl 3-Hydroxyphenylacetate

Product 1

HCID 57431972HCID 57431972, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (3-Hydroxy-phenyl)-acetic acid methyl ester (5.5 g, 33.1 mmol), N,N-dimethyl thiocarbamoyl chloride (5.11 g, 41.38 mmol), triethylamine (9.2 mL, 66.2 mmol), N,N-dimethylamino pyridine (0.4 g, 3.31 mmol) and dioxane (50 mL) is stirred at reflux 18 hr. The mixture is concentrated, partioned between 1M aqueous hydrochloric acid (200 mL) and ethyl acetate (3×75 mL). The combined organic extracts are dried over anhydrous magnesium sulfate, filtered, concentrated, and purified via silica chromatography eluting the product with dichloromethane to afford the title compound as a brown oil, 6.8 g, 81%. MS M++1 254. The structure is confirmed by 1H NMR spectroscopy.

Workup

  1. temperatureat reflux 18 hr
  2. concentrationThe mixture is concentrated
  3. dry with materialThe combined organic extracts are dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified via silica chromatography
  7. washeluting the product with dichloromethane

Sources & evidence

ORD record
ord-a539154878a44ab48073b3ad01cc34a6
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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