Benzenesulfonyl chloride → Methyl 5-phenyl-1-(phenylsulfonyl)-4-propyl-1H-pyrrole-3-carboxylate

HRID 554270Notes

Reaction equation

[C:1]1([C:7]2[NH:11][CH:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[C:8]=2[CH2:16][CH2:17][CH3:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[C:1]1([C:7]2[N:11]([S:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:29])=[O:28])[CH:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[C:8]=2[CH2:16][CH2:17][CH3:18])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 3

HCID 7369Benzenesulfonyl chloride

HCID 24758Sodium hydride

HCID 66924692Methyl 5-phenyl-4-propyl-1H-pyrrole-3-carboxylate

Product 1

HCID 66924675Methyl 5-phenyl-1-(phenylsulfonyl)-4-propyl-1H-pyrrole-3-carboxylateYield 86.6%

Procedure

Using methyl 5-phenyl-4-propyl-1H-pyrrole-3-carboxylate (2.0 g), sodium hydride (60% in oil, 434 mg) and benzenesulfonyl chloride (1.60 g), a procedure as in Reference Example 4 was performed to give the title compound as colorless crystals (yield 2.73 g, 69%).

Sources & evidence

ORD record: ord-4e313a3bbad2443a828584e9ada24721
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048909B2

Reaction notes

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