Allyl bromide → 1-Allyl-N-tert-butylcyclopropane-1-sulfonamide

Reaction equation

[C:1]([NH:5][S:6]([C:9]1([CH3:12])[CH2:11][CH2:10]1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:13](Br)[CH:14]=C>>[C:1]([NH:5][S:6]([C:9]1([CH2:12][CH:13]=[CH2:14])[CH2:11][CH2:10]1)(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 7841Allyl bromide

HCID 21889792N-tert-butyl-1-methylcyclopropane-1-sulfonamide

Product 1

HCID 218897951-Allyl-N-tert-butylcyclopropane-1-sulfonamideYield 97%

Procedure

This compound was obtained in 97% yield according to the procedure described in the synthesis of N-tert-butyl-(1-methyl)cyclopropylsulfonamide using 1.25 equivalents of allyl bromide as the electrophile. The compound was used in the next reaction without further purification: 1H NMR (CDCl3) δ 0.83 (m, 2H), 1.34 (s, 9H), 1.37 (m, 2H), 2.64 (d, J=7.3 Hz, 2H), 4.25 (br s, 1H), 5.07-5.10 (m, 2H), 6.70-6.85 (m, 1H).

Workup

customThis compound was obtained in 97% yield
customThe compound was used in the next reaction without further purification

Sources & evidence

ORD record: ord-6bb21f6ab41e4a568bc7207e94a041d6
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888464B2

Reaction notes

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