Benzyl Bromide → 1-Benzyl-N-tert-butylcyclopropane-1-sulfonamide

HRID 500327Notes

Reaction equation

HRID 500327 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].C(Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCC)(=O)C>CCCCCC>[C:1]([NH:5][S:6]([C:9]1([CH2:12][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][CH2:10]1)(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 21889792N-tert-butyl-1-methylcyclopropane-1-sulfonamide

Product 1

HCID 218897961-Benzyl-N-tert-butylcyclopropane-1-sulfonamideYield 60%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

This compound was obtained in 60% yield using the procedure described for the synthesis of N-tert-butyl-(1-methyl)cyclopropylsulfonamide except 1.05 equivalents of benzyl bromide were used, followed by trituration with 10% ethyl acetate in hexane: 1H NMR (CDCl3) δ 0.92 (m, 2H), 1.36 (m, 2H), 1.43 (s, 9H), 3.25 (s, 2H), 4.62 (br s, 1H), 7.29-7.36 (m, 5H).

Workup

  1. customThis compound was obtained in 60% yield

Sources & evidence

ORD record
ord-c98f49bca4274f19ba2f91084d747ef4
Source dataset
uspto-grants-2010_08
Patent number
US07772180B2

Reaction notes

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