Methyl Benzoate → 1-Benzoyl-N-tert-butylcyclopropane-1-sulfonamide

HRID 544828Notes

Reaction equation

HRID 544828 reaction equation
[C:1]([NH:5][S:6]([C:9]1(C)[CH2:11][CH2:10]1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:13]([O:21]C)(=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:1]([NH:5][S:6]([C:9]1([C:13](=[O:21])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:11][CH2:10]1)(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 7150Methyl BenzoateHCID 21889792N-tert-butyl-1-methylcyclopropane-1-sulfonamide

Product 1

HCID 218898301-Benzoyl-N-tert-butylcyclopropane-1-sulfonamideYield 66%

Procedure

This compound was obtained in 66% yield using the procedure described for the synthesis of N-tert-butyl-(1-methyl)cyclopropylsulfonamide using 1.2 equivalents of methyl benzoate as the electrophile. The crude product was purified by column chromatography over SiO2 using 30% to 100% dichloromethane in hexane: 1H NMR (CDCl3) δ 1.31 (s, 9H), 1.52 (m, 2H), 1.81 (m, 2H), 4.16 (br s, 1H), 7.46 (m, 2H), 7.57 (m, 1H), 8.05 (d, J=8.5 Hz, 2H).

Workup

  1. customThis compound was obtained in 66% yield
  2. customThe crude product was purified by column chromatography over SiO2 using 30% to 100% dichloromethane in hexane

Sources & evidence

ORD record
ord-63b0dba5dda540d7aa9ee481fbc6ffe0
Source dataset
uspto-grants-2011_05
Patent number
US07935670B2

Reaction notes

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