N-Methylbenzylamine → Tert-butyl {[benzyl(methyl)amino]sulfonyl}carbamate

HRID 222268Notes

Reaction equation

HRID 222268 reaction equation
[C:1]([O:5][C:6]([N-:8][S:9](N1C=CC(=[N+](C)C)C=C1)(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21][NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[CH2:23]([N:22]([CH3:21])[S:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])(=[O:10])=[O:11])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 7669N-MethylbenzylamineHCID 178482962HCID 178482962, compound

Product 1

HCID 57526684Tert-butyl {[benzyl(methyl)amino]sulfonyl}carbamateYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-dialkyl sulfamides were prepared according to the published procedures: Winum, J-Y; Toupet, L.; Barragan, V.; Dewynter, G.; Montero, J.-L. Org. Letters 2001, 3, 2241-2243 and Casini, A.; Winum, J.-Y.; Montero, J.-L.; Scozzafava, A.; Supuran, C. Bioorganic & Medicinal Chemistry Letters 2003, 13, 837-840. A flask was charged with N-tert-butoxycarbonyl-N-[4-(dimethylazaniumylidene)-1,4-dihydropyridin-1-ylsulfonyl]azanide (500 mg, 1.66 mmol) and methylbenzylamine (0.21 mL, 1.66 mmol) in 10 mL of CH2Cl2. After 2 h, the solution was concentrated in vacuo and purified by flash column chromatography (5-70% EtOAc/hexanes) to afford 304 mg of tert-butyl {[benzyl(methyl)amino]sulfonyl}carbamate.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. custompurified by flash column chromatography (5-70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-69b25653010546b197cce39dca92644c
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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