Sulfuric Acid → HCID 59717855, compound

HRID 601579Notes

Reaction equation

HRID 601579 reaction equation
[CH3:1][Li].[CH2:3]([NH:10][CH2:11][CH2:12][C:13]1[CH:27]=[CH:26][C:16]([O:17][C:18]2[CH:25]=[CH:24][C:21](C#N)=[CH:20][CH:19]=2)=[CH:15][CH:14]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.S(=O)(=O)(O)O.[C:33](=[O:36])(O)[O-].[Na+]>C(OCC)C.O1CCCC1>[CH2:3]([NH:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][C:18]2[CH:25]=[CH:24][C:21]([C:33](=[O:36])[CH3:1])=[CH:20][CH:19]=2)=[CH:26][CH:27]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 59717848HCID 59717848, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 59717855HCID 59717855, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1.4M Methyl Lithium in diethyl ether was added to a dry flask then cooled to 0° C. A solution of 4-[4-(2-Benzylamino-ethyl)-phenoxy]-benzonitrile (2.5 g, 7.6 mmol) (see example 4) in dry tetrahydrofuran (25 mL) was added dropwise to the reaction then stirred at 0° C. for 60 minutes. 3M Sulfuric Acid (12.7 mL, 38 mmol) was added dropwise then the reaction was heated at 50° C. for 3 hours. The reaction was cooled to room temperature then poured into saturated aqueous sodium bicarbonate solution then extracted with dichloromethane (3×75 mL). The combined dichloromethane extracts were dried over sodium chloride/magnesium sulfate, filtered, and concentrated on a rotary evaporator to yield 3.1 g of crude product, which was purified by flash column chromatography on silica gel eluting with ethanol in dichloromethane to yield 1-{4-[4-(2-Benzylamino-ethyl)-phenoxy]-phenyl}-ethanone (0.6 g) which was used directly in the next step.

Workup

  1. temperaturethe reaction was heated at 50° C. for 3 hours
  2. temperatureThe reaction was cooled to room temperature
  3. extractionthen extracted with dichloromethane (3×75 mL)
  4. dry with materialThe combined dichloromethane extracts were dried over sodium chloride/magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated on a rotary evaporator
  7. customto yield 3.1 g of crude product, which
  8. customwas purified by flash column chromatography on silica gel eluting with ethanol in dichloromethane

Sources & evidence

ORD record
ord-ea6f79c9e3b143dd944668cd1fc36c89
Source dataset
uspto-grants-2011_03
Patent number
US07902372B2

Reaction notes

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