Chlorosuccinimide → HCID 10832560, compound

HRID 1585080Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[CH:11][CH:10]=[C:9]2[CH3:23])=[CH:4][CH:3]=1.[Cl:24]N1C(=O)CCC1=O>C1COCC1>[Cl:24][C:10]1[CH:11]=[C:12]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:9]=1[CH3:23]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole (Example 1) (1 g, 3.03 mmol) in THF (100 ml) at -70° C., N-chlorosuccinimide (488 mg, 3.65 mmol) was added over 10 minutes. The reaction mixture was warmed to 20° C. over 3 hours and stirred for 18 hours. More N-chlorosuccinimide (450 mg, 3.37 mmol) was added and the mixture was stirred for 6 hours. After dilution with aqueous potassium carbonate, the reaction mixture was extracted with ethyl acetate. The organic fractions were washed with water, dried (MgSO4), filtered and concentrated. The crude dark orange solid (1.3 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 1/1) to give 3-chloro-1-(4-fluorophenyl)-2-methyl-5-[-4-(methylsulfonyl)phenyl]-1H-pyrrole (107 mg, 10%): mp (DSC) 172° C. Anal Calc'd. for C18H15NSClFO2 : C, 59.42; H, 4.16; N, 3.85. Found: C, 59.21; H, 4.10; N, 3.56.

Workup

stirringthe mixture was stirred for 6 hours
extractionAfter dilution with aqueous potassium carbonate, the reaction mixture was extracted with ethyl acetate
washThe organic fractions were washed with water
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe crude dark orange solid (1.3 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 1/1)

Sources & evidence

ORD record: ord-0c4f1b2523914f1a9ab540be8ec51a4e
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05935990

Reaction notes

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