1-Methylcyclopropane-1-sulfonamide → 1-Benzoylcyclopropane-1-sulfonamide

HRID 1818758Notes

Reaction equation

HRID 1818758 reaction equation
C([NH:5][S:6]([C:9]1([C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10]1)(=[O:8])=[O:7])(C)(C)C.CC1(S(N)(=O)=O)CC1>>[C:12]([C:9]1([S:6]([NH2:5])(=[O:8])=[O:7])[CH2:10][CH2:11]1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 218898141-Methylcyclopropane-1-sulfonamideHCID 218898301-Benzoyl-N-tert-butylcyclopropane-1-sulfonamide

Product 1

HCID 218897941-Benzoylcyclopropane-1-sulfonamideYield 87%

Procedure

This compound was obtained in 87% yield from N-tert-butyl(1-benzoyl)cyclopropyl-sulfonamide (from Step A.6.a) using the procedure described for the synthesis of 1-methylcyclopropylsulfonamide, followed by recrystallization from the minimum amount of ethyl acetate in hexane: 1H NMR (DMSO-d6) δ 1.39 (m, 2H), 1.61 (m, 2H), 7.22 (s, 2H), 7.53 (t, J=7.6 Hz, 2H), 7.65 (t, J=7.6 Hz, 1H), 8.06 (d, J=8.2 Hz, 2H); 13C NMR (DMSO-d6) δ 12.3, 48.4, 128.1, 130.0, 133.4, 135.3, 192.0.

Workup

  1. customfollowed by recrystallization from the minimum amount of ethyl acetate in hexane

Sources & evidence

ORD record
ord-61e95e15f103478c8136d56a7e741f41
Source dataset
uspto-grants-2009_10
Patent number
US07601686B2

Reaction notes

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