Tert-butyl {[methyl(tetrahydrofuran-3-yl)amino]sulfonyl}carbamate → N-methyl-N-(tetrahydrofuran-3-yl)sulfamide

HRID 222282Notes

Reaction equation

HRID 222282 reaction equation
[CH3:1][N:2]([CH:14]1[CH2:18][CH2:17][O:16][CH2:15]1)[S:3]([NH:6]C(=O)OC(C)(C)C)(=[O:5])=[O:4]>C(Cl)Cl.FC(F)(F)C(O)=O>[CH3:1][N:2]([CH:14]1[CH2:18][CH2:17][O:16][CH2:15]1)[S:3]([NH2:6])(=[O:5])=[O:4]

Participants

4

Reactant 1

HCID 86609783Tert-butyl {[methyl(tetrahydrofuran-3-yl)amino]sulfonyl}carbamate

Product 1

HCID 67364770N-methyl-N-(tetrahydrofuran-3-yl)sulfamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-butyl {[methyl(tetrahydrofuran-3-yl)amino]sulfonyl}carbamate (1.47 g, 5.23 mmol) was dissolved in 70 mL of CH2Cl2 and 45 mL of trifluoroacetic acid. After 1 h the solution was concentrated in vacuo, diluted in CH2Cl2, washed with saturated aqueous NaHCO3 and brine, then dried over Na2SO4. The solution was concentrated in vacuo to afford the title compound. 1H NMR (600 MHz, DMSO-d6) δ 4.25-4.31 (m, 1H); 3.79-3.84 (m, 1H); 3.58-3.66 (m, 2H); 3.47-3.52 (m, 1H); 2.56 (s, 3H), 2.04-2.10 (m, 1H); 1.81-1.88 (m, 1H).

Workup

  1. concentrationAfter 1 h the solution was concentrated in vacuo
  2. additiondiluted in CH2Cl2
  3. washwashed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-fa40a43cb5d14beea44c48174e127989
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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