Pyridine → Methyl 3-(4-tert-butylphenylsulfonamido)thiophene-2-carboxylate

HRID 1925704

Reaction equation

[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].[C:11]([C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].N1C=CC=CC=1>Cl>[C:11]([C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:1][C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7]([O:9][CH3:10])=[O:8])(=[O:23])=[O:22])=[CH:17][CH:16]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

Conditions

Temperature: 65 °C

Procedure

In an appropriate vessel, methyl 3-aminothiophene-2-carboxylate (2.5 g; 15.9 mmol) was combined with 4-tert-butylbenzene sulfonyl chloride (3.70 g; 15.9 mmol) and dissolved by addition of pyridine (5.00 mL; 63.2 mmol). The reaction mixture was heated at 65° C. for 2 hours cooled to room temperature, diluted with aqueous hydrochloric acid (100 mL; 2M) and extracted with dichloromethane (3×30 mL). The combined organic extracts were washed with aqueous hydrochloric acid (100 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting crude solid was recrystallized from a minimal amount of isopropanol to give the title product as a yellow solid (5.2 g).

Workup

temperaturecooled to room temperature
extractionextracted with dichloromethane (3×30 mL)
washThe combined organic extracts were washed with aqueous hydrochloric acid (100 mL)
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting crude solid was recrystallized from a minimal amount of isopropanol

Sources & evidence

ORD record: ord-99d88049fc4f408e9f63ac647e8fb6b1
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178699B2

Linked notes

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