Benzenesulfonyl chloride → HCID 20043757, compound

HRID 1761887Notes

Reaction equation

HRID 1761887 reaction equation
[CH2:1]([O:4][CH:5]1[NH:9][C:8](=[O:10])[CH2:7][CH2:6]1)[CH:2]=C.[C:11]1([S:17](Cl)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:21](OCC)(=O)C>CCOCC>[C:11]1([S:17]([N:9]2[CH:5]([O:4][C:1]([CH3:2])=[CH2:21])[CH2:6][CH2:7][C:8]2=[O:10])(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 15078420HCID 15078420, compound

Product 1

HCID 20043757HCID 20043757, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

The operation is done as in example 49, starting with 0.80 g of 5-(2-propenyloxy)pyrrolidin-2-one. After cooling to -10° C., a solution of 1.00 g of benzenesulphonyl chloride in 10 cm3 of anhydrous ether is added and the temperature is maintained at -10° C. 100 cm3 of ethyl acetate is added before filtering. Elution is done with a mixture of ethyl acetate and hexane (1-1) and by re-crystallizing from isopropyl ether, 0.20 g of product is obtained, m.p. 54°-56° C.

Workup

  1. temperaturethe temperature is maintained at -10° C
  2. filtrationbefore filtering
  3. washElution
  4. additionis done with a mixture of ethyl acetate and hexane (1-1)
  5. customby re-crystallizing from isopropyl ether

Sources & evidence

ORD record
ord-c3651c3b89474fd09deb35af71cec040
Source dataset
uspto-grants-1989_05
Patent number
US04829079

Reaction notes

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