Hydrochloric Acid → HCID 59648376, compound

HRID 251886Notes

Reaction equation

HRID 251886 reaction equation
[S:1]([NH2:5])([NH2:4])(=[O:3])=[O:2].[H-].[Na+].Br[CH2:9][CH2:10][CH2:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>CN(C=O)C>[CH2:13]([O:12][CH2:11][CH2:10][CH2:9][NH:4][S:1]([NH2:5])(=[O:3])=[O:2])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 82267SulfamideHCID 2776064Benzyl 3-Bromopropyl Ether

Product 1

HCID 59648376HCID 59648376, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of sulfamide (1.0 g, 10.4 mmol) in dry DMF (50 mL) is added NaH (416 mg 60% dispersion in mineral oil, 10.4 mmol) in portions. After the evolution of gas has stopped, (3-bromo-propoxymethyl)-benzene (2.38 g, 10.4 mmol) is added and the reaction mixture is stirred at 50° C. for 18 h. The suspension is cooled to rt, neutralized with 1N aq. HCl (5 mL) and concentrated. The solid residue is suspended in acetone and filtered. The filtrate is evaporated and the residue is purified by column chromatography on silica gel eluting with hexane/EA to afford 3-benzyloxypropylsulfamide (651 mg) as a colourless oil. LC-MS: tR=0.73 min, [M+H]+=245.18; 1H NMR (CDCl3): δ 7.39-7.27 (m, 5H), 4.94 (t br, J=4.6 Hz, 1H), 4.53 (s br, 2H), 4.50 (s, 2H), 3.60 (t, J=5.9 Hz, 2H), 3.26 (q, J=5.9 Hz, 2H), 1.89 (p, J=5.9 Hz, 2H).

Workup

  1. temperatureThe suspension is cooled to rt
  2. concentrationconcentrated
  3. filtrationfiltered
  4. customThe filtrate is evaporated
  5. customthe residue is purified by column chromatography on silica gel eluting with hexane/EA

Sources & evidence

ORD record
ord-fba3877a69b84f158cca7d2b441bab2b
Source dataset
uspto-grants-2011_01
Patent number
US07868012B2

Reaction notes

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