Triethylamine → N-Cyclobutyl-2-nitrobenzene-1-sulfonamide

HRID 1487229Notes

Reaction equation

HRID 1487229 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].C(N(CC)CC)C.[CH:21]1([NH2:25])[CH2:24][CH2:23][CH2:22]1>ClCCl>[CH:21]1([NH:25][S:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 75645Cyclobutylamine

Product 1

HCID 68284532N-Cyclobutyl-2-nitrobenzene-1-sulfonamideYield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-nitrobenzene-1-sulfonyl chloride (6.8 g, 30.8 mol) in dichloromethane (100 mL) at 0° C. was added triethylamine (14 g, 138.6 mol) and cyclobutanamine (2.2 g, 31 mmol) in several portions over 10-15 minutes. The reaction mixture was stirred at room temperature for 4 hours, concentrated and purified by silica gel chromatography to afford the product N-cyclobutyl-2-nitrobenzenesulfonamide (7 g, yield 88.9%). 1H NMR (400 MHz, CDCl3) δ ppm 8.14-8.16 (m, 1H), 7.84-7.87 (m, 1H), 7.72-7.74 (m, 2H), 5.45-5.47 (d, 1H, J=8.8 Hz), 3.93-3.99 (m, 1H), 2.11-2.18 (m, 2H), 1.84-1.90 (m, 2H), 1.59-1.69 (m, 2H).

Workup

  1. concentrationconcentrated
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-600c617f08a74c698634866c2d87d64e
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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