Bromine → N-[4-(Bromoacetyl)phenyl]-N'-tert.-butylsulfamide

HRID 442256Notes

Reaction equation

HRID 442256 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])=[O:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br:19]Br>BrBr.O1CCOCC1>[Br:19][CH2:2][C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][S:11]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])=[O:12])=[CH:8][CH:9]=1)=[O:3]

Participants

5

Reactant 2

HCID 24408BromineHCID 21416935N-(4-acetylphenyl)-N'-tert.-butylsulfamide

Product 1

HCID 21416979N-[4-(Bromoacetyl)phenyl]-N'-tert.-butylsulfamide

Reagents, catalysts & solvents 2

HCID 24408BromineCatalystHCID 312751,4-DioxaneSolvent

Procedure

A few drops of bromine (from a total of 10.3 g., 0.064 mole) is added to N-(4-acetylphenyl)-N'-tert.-butylsulfamide (17.3 g., 0.064 mole) in dioxane (200 ml.) solution at 15° C. and the solution is stirred until the color is discharged. The remainder of the bromine is added during 5 min. and the solution is stirred for an additional 10 min. thereafter. The solution is concentrated in vacuo and the residue triturated with isopropyl ether to give 20.7 g. (92%) of intermediate, recrystallized from isopropanol, m.p. 160.5°-161° C. (dec.)

Workup

  1. stirringthe solution is stirred for an additional 10 min.
  2. concentrationThe solution is concentrated in vacuo
  3. customthe residue triturated with isopropyl ether
  4. customto give 20.7 g
  5. custom(92%) of intermediate, recrystallized from isopropanol, m.p. 160.5°-161° C. (dec.)

Sources & evidence

ORD record
ord-fcb7e3b91a394155a2661f7ee13a51b2
Source dataset
uspto-grants-1977_08
Patent number
US04044151

Reaction notes

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