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

HRID 1925707

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.ClCCl>[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: 40 °C

Procedure

To a solution of methyl 3-aminothiophene-2-carboxylate (0.55 g; 3.5 mmol) in pyridine (2 mL) and dichloromethane (2 mL) was added 4-tert-butylbenzenesulfonyl chloride (0.98 g; 4.2 mmol). The resulting mixture was warmed to 40° C. to aid in solubility, then stirred at room temperature for 48 hours. The reaction mixture was diluted with dichloromethane and washed with aqueous hydrochloric acid (2N). The aqueous layer was separated and extracted with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, decanted, and filtered through a and of silica. The silica was washed with dichloromethane. The eluant was combined with hexanes and allowed to stand. After 24 hours the resulting solid product was collected by filtration to give the desired product as a white solid (817 mg).

Workup

washwashed with aqueous hydrochloric acid (2N)
customThe aqueous layer was separated
extractionextracted with dichloromethane
dry with materialdried over anhydrous sodium sulfate
customdecanted
filtrationfiltered through a and of silica
washThe silica was washed with dichloromethane
filtrationAfter 24 hours the resulting solid product was collected by filtration

Sources & evidence

ORD record: ord-4fc1342cfdfe4611b700d4c23e1bcb89
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178699B2

Linked notes

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