Dicyclohexylcarbodiimide → 2-Pyrrolidinone, 1-((4-chlorophenyl)sulfonyl)-

HRID 1762457

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:12][CH2:13][CH2:14][C:15]2=[O:17])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In 20 ml of tetrahydrofuran was dissolved 2.78 g of N-(4'-chlorobenzenesulfonyl)-4-aminobutyric acid (0.01 mole). To the stirred solution on an ice bath was added 2.06 g of dicyclohexylcarbodiimide (0.01 mole), and the mixture was stirred at 0° C. for 21 hours. The reaction mixture was filtered, and the solid material was washed with anhydrous tetrahydrofuran. The filtrate and the washings were combined, and tetrahydrofuran was removed under reduced pressure. The residue thus obtained was recrystallized from a mixed solvent of chloroform-ether to give 2.37 g of N-(4'-chlorobenzenesulfonyl)-2-pyrrolidone as crystals. Physical properties were identical with those in Synthetic Example 3.

Workup

filtrationThe reaction mixture was filtered
washthe solid material was washed with anhydrous tetrahydrofuran
customtetrahydrofuran was removed under reduced pressure
customThe residue thus obtained
customwas recrystallized from a mixed solvent of chloroform-ether

Sources & evidence

ORD record: ord-4e17afe515de4ed6bdec791d6f3984de
Source dataset: uspto-grants-1989_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04833156

Linked notes

Loading…