Sulfamide → HCID 58244794, compound

HRID 1486417Notes

Reaction equation

HRID 1486417 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].[S:15](=[O:19])(=[O:18])(N)[NH2:16]>O1CCOCC1.C(OC(C)C)(C)C>[C:10]([O:9][C:8](=[O:14])[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][N:2]([S:15]([NH2:16])(=[O:19])=[O:18])[CH3:1])([CH3:11])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 82267SulfamideHCID 20709354tert-Butyl [4-(methylamino)butyl]carbamate

Product 1

HCID 58244794HCID 58244794, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 7914Diisopropyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl 4-(methylamino)butylcarbamate (4 g, 19.77 mmoles) and sulfuric diamide (7.6 g, 4 eq) in dioxane (10 mL) was heated at 100° C. in a microwave oven during 30 minutes. The RM was then concentrated in vacuo, and DCM was added. The resulting white precipitate of sulfuric diamide in excess was filtered off, and the filtrate was successively washed with diluted HCl, then brine, dried over magnesium sulfate, filtered and concentrated. Trituration in diisopropyl ether afforded 3.55 g (64% yield) of tert-butyl 4-(methyl(sulfamoyl)amino)butylcarbamate 10b as a white solid; m/z 282 [M+H]+.

Workup

  1. concentrationThe RM was then concentrated in vacuo, and DCM
  2. additionwas added
  3. filtrationThe resulting white precipitate of sulfuric diamide in excess was filtered off
  4. washthe filtrate was successively washed with diluted HCl
  5. dry with materialbrine, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-05444cfb4f0f428496e640a833731fa2
Source dataset
uspto-grants-2016_08
Patent number
US09427440B2

Reaction notes

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