Acetone → N-[4-(N-benzyl-N-isopropylglycyl)phenyl]-N'-tert.-butylsulfamide hydrobromide

HRID 442258Notes

Reaction equation

HRID 442258 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([NH:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:14])=[O:13])=[CH:7][CH:6]=1)=[O:4].CC(C)=O.[CH2:24]([NH:31][CH:32]([CH3:34])[CH3:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CCOCC>[BrH:1].[CH2:24]([N:31]([CH:32]([CH3:34])[CH3:33])[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([NH:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:14])=[O:13])=[CH:7][CH:6]=1)=[O:4])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 66024IsopropylbenzylamineHCID 21416979N-[4-(Bromoacetyl)phenyl]-N'-tert.-butylsulfamide

Product 1

HCID 21416939N-[4-(N-benzyl-N-isopropylglycyl)phenyl]-N'-tert.-butylsulfamide hydrobromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The intermediate of Procedure 4 (10.0 g., 0.029 mole) is added portion-wise to an acetone solution (100 ml.) of benzylisopropylamine (9.0 g., 0.06 mole). The mixture is stirred for 5 hr. and then diluted with ether (400 ml.) to precipitate 4.9 g. of insoluble by-product benzylisopropylamine hydrobromide which is filtered and discarded. The filtrate is acidified with ethanolic hydrogen bromide to yield 13 g. (89%) of desired intermediate recrystallized from 95% ethanol, m.p. 195.5°-196.5° C. (dec.).

Workup

  1. customto precipitate 4.9 g
  2. filtrationof insoluble by-product benzylisopropylamine hydrobromide which is filtered
  3. customto yield 13 g
  4. custom(89%) of desired intermediate recrystallized from 95% ethanol, m.p. 195.5°-196.5° C. (dec.)

Sources & evidence

ORD record
ord-f4cff5e9b37c4ea2bdc26449368e8ca6
Source dataset
uspto-grants-1977_08
Patent number
US04044151

Reaction notes

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