Sodium Hydroxide → 1-((4-(2-(crotonylamino)ethyl)phenyl)sulfonyl)-3-cyclohexyl-2-iminoimidazolidine

HRID 280875Notes

Reaction equation

HRID 280875 reaction equation
Cl.[CH:2]1([N:8]2[CH2:12][CH2:11][NH:10][C:9]2=[NH:13])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[OH-].[Na+].[C:16]([NH:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1)(=[O:20])/[CH:17]=[CH:18]/[CH3:19]>O.CC(C)=O>[C:16]([NH:21][CH2:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([S:30]([N:10]2[CH2:11][CH2:12][N:8]([CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]3)[C:9]2=[NH:13])(=[O:32])=[O:31])=[CH:28][CH:29]=1)(=[O:20])/[CH:17]=[CH:18]/[CH3:19]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 23320218HCID 23320218, compoundHCID 178479146HCID 178479146, compound

Product 1

HCID 63667971-((4-(2-(crotonylamino)ethyl)phenyl)sulfonyl)-3-cyclohexyl-2-iminoimidazolidine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

20.4 g of 1-cyclohexyl-2-imino-imidazolidine hydrochloride are added to 8.5 g of sodium hydroxide in 85 ml of water. There is added to the resulting solution 28.8 g of 4-(2-crotonylaminoethyl)-benzenesulphonyl chloride dissolved in 100 ml of acetone, the reaction mixture becoming warm. It is heated at 90° for half an hour and then concentrated by evaporation under reduced pressure. The residue is recrystallised from ethyl acetate, and 1-{4-[2-(crotonylamino)-ethyl]-phenylsulphonyl}-3-cyclohexyl-2-imino-imidazolidine (trans) which melts at 157° to 158° is obtained.

Workup

  1. temperaturethe reaction mixture becoming warm
  2. temperatureIt is heated at 90° for half an hour
  3. concentrationconcentrated by evaporation under reduced pressure
  4. customThe residue is recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-964f817e8d434458b2e2bb4845ce61bb
Source dataset
uspto-grants-1986_05
Patent number
US04591597

Reaction notes

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