Diethyl Sulfate → HCID 15672496, compound

HRID 1111066Notes

Reaction equation

HRID 1111066 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:9]2[C:10](=[O:18])[CH:11]([CH2:15][CH2:16][CH3:17])[CH2:12][C:13]=2[NH2:14])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].S(OCC)(O[CH2:27][CH3:28])(=O)=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[F:1][C:2]([F:19])([F:20])[C:3]1[CH:4]=[C:5]([C:9]2[C:10](=[O:18])[CH:11]([CH2:15][CH2:16][CH3:17])[CH2:12][C:13]=2[NH:14][CH2:27][CH3:28])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 6163Diethyl SulfateHCID 14798Sodium HydroxideHCID 15672495HCID 15672495, compound

Product 1

HCID 15672496HCID 15672496, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

In this example, a mixture containing 8.0 g of 2-(3-trifluoromethylphenyl)-3-amino-5-propyl-2-cyclopentenone; 3.0 g of aqueous 50 wt % sodium hydroxide; 6.4 g of benzyltriethylammonium chloride; and 5.0 ml of diethyl sulfate in 70 ml of methylene chloride was stirred at room temperature for about 1 hour and then warmed to, and stirred at reflux for about 15 to 20 minutes. The mixture was cooled to room temperature and successively washed three times with water, twice with aqueous 1N hydrochloric acid and then twice with saturated aqueous sodium bicarbonate. The washed mixture was dried over magnesium sulfate and evaporated affording an oil residue. The oil was triturated with a mixture of ethyl ether and petroleum ethers and filtered affording 3.2 g of the title compound as a solid, m.p. 120°-120.5° C.

Workup

  1. temperaturewarmed to, and
  2. temperatureat reflux for about 15 to 20 minutes
  3. washsuccessively washed three times with water
  4. dry with materialThe washed mixture was dried over magnesium sulfate
  5. customevaporated
  6. customaffording an oil residue
  7. customThe oil was triturated with a mixture of ethyl ether and petroleum ethers
  8. filtrationfiltered

Sources & evidence

ORD record
ord-df216bd2a9514bb587dd01eb8776ac4e
Source dataset
uspto-grants-1990_12
Patent number
US04978386

Reaction notes

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