Dichloromethane → HCID 67345859, compound

HRID 1669400Notes

Reaction equation

HRID 1669400 reaction equation
[S:1](N)([NH2:4])(=[O:3])=[O:2].[CH:6]1([CH2:9][NH:10][CH2:11][CH:12]([O:15][CH3:16])[O:13][CH3:14])[CH2:8][CH2:7]1.C(Cl)Cl>O1CCOCC1>[CH:6]1([CH2:9][N:10]([CH2:11][CH:12]([O:13][CH3:14])[O:15][CH3:16])[S:1]([NH2:4])(=[O:3])=[O:2])[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 82267SulfamideHCID 457925181104193-66-9

Product 1

HCID 67345859HCID 67345859, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sulfamide (5 eq) was added to a solution of N-(cyclopropylmethyl)-(2,2-dimethoxyethanamine) in dioxane (0.12 M). The reaction was stirred at reflux overnight. The solvent was removed in vacuo, the residue taken up in EtOAc and washed with H2O, brine, before being dried (Na2SO4), filtered and concentrated in vacuo to give the crude material. DCM was added and the resultant precipitate removed by filtration, while the filtrate was concentrated in vacuo to afford the product (68%). 1H NMR (300 MHz, DMSO-d6, 300 K) δ 0.15-0.19 (m, 2H), 0.44-0.47 (m, 2H), 1.03-1.05 (m, 1H), 2.95-2.98 (m, 2H), 3.17-3.19 (m, 2H), 3.28 (s, 6H), 4.51 (t, J 5.0, 1H), 6.63 (s, 2H).

Workup

  1. temperatureat reflux overnight
  2. customThe solvent was removed in vacuo
  3. washwashed with H2O, brine
  4. dry with materialbefore being dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the crude material
  8. customthe resultant precipitate removed by filtration, while the filtrate
  9. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-16e70f4f07b14205afdef4fd1c776548
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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