Sulfur Dioxide → 2-aminosulfonyl-6-sec-butyl-4-methoxy-N,N-diethylbenzamide

HRID 1768709Notes

Reaction equation

CN(C)CCN(C)C.C([Li])(CC)C.[CH:14]([C:18]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:19]=1[C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:21])([CH2:16][CH3:17])[CH3:15].[S:33](=[O:35])=[O:34].S(Cl)(Cl)(=O)=O.[OH-].[NH4+:42]>C1COCC1>[NH2:42][S:33]([C:27]1[CH:28]=[C:29]([O:31][CH3:32])[CH:30]=[C:18]([CH:14]([CH2:16][CH3:17])[CH3:15])[C:19]=1[C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:21])(=[O:35])=[O:34]

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of tetramethylethylenediamine (31 mL) in THF (500 mL) at -78° C. was added sec-butyllithium (170 mL, 1.1M), followed by 2-sec-butyl-4-methoxy-N,N-diethylbenzamide (45 g) in THF (150 mL). The mixture was stirred at -78° for 15 minutes, then at 0° C. for 30 minutes, then sulfur dioxide (50 mL) was condensed into the mixture at -78° C. The mixture was warmed to -10° C., sulfuryl chloride (17 mL) was added and then the mixture was slowly warmed to room temperature and stirred overnight. The reaction mixture was added to a solution of ammonium hydroxide (94 mL) in THF (200 mL), the mixture was filtered through a pad of silica/Na2SO4 /sand to afford 51.8 g of 2-aminosulfonyl-6sec-butyl-4-methoxy-N,N-diethylbenzamide.

Workup

waitat 0° C. for 30 minutes
customcondensed into the mixture at -78° C
temperaturethe mixture was slowly warmed to room temperature
stirringstirred overnight
filtrationthe mixture was filtered through a pad of silica/Na2SO4 /sand

Sources & evidence

ORD record: ord-48466708a3e142baac4c8844a95e6aa7
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05378720

Reaction notes

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