Sodium Hydroxide → HCID 21555926, compound

HRID 267240Notes

Reaction equation

HRID 267240 reaction equation
[OH-].[Na+].Cl.[CH:4]1([N:10]2[CH2:14][CH2:13][NH:12][C:11]2=[NH:15])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[C:16]([NH:21][CH2:22][CH2:23][C:24]1[S:28][C:27]([S:29](Cl)(=[O:31])=[O:30])=[CH:26][CH:25]=1)(=[O:20])[CH2:17][CH2:18][CH3:19]>O.CC(C)=O>[C:16]([NH:21][CH2:22][CH2:23][C:24]1[S:28][C:27]([S:29]([N:12]2[CH2:13][CH2:14][N:10]([CH:4]3[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]3)[C:11]2=[NH:15])(=[O:31])=[O:30])=[CH:26][CH:25]=1)(=[O:20])[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21555929HCID 21555929, compoundHCID 178479146HCID 178479146, compound

Product 1

HCID 21555926HCID 21555926, compound

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

20 ml (0.02 mol) of 1 N sodium hydroxide solution are added dropwise over the course of 10 minutes, whilst stirring, to a mixture of 2.04 g (0.01 mol) of 1-cyclohexyl-2-imino-imidazolidine hydrochloride and 2.96 g (0.01 mol) of 5-(2-butyramido-ethyl)-2-thiophenesulphonyl chloride in 45 ml of water-acetone (1:2), at 25°C. In the course thereof, the reaction temperature rises to 33°C. The reaction mixture is stirred for a further 18 hours at 24°-25°C and the acetone is then evaporated off with the aid of a rotary evaporator. The oil-water mixture which remains is extracted twice with 30 ml of ethyl acetate at a time. The extracts are washed with 20 ml of saturated sodium chloride solution, then combined, dried over sodium sulphate and evaporated in vacuo. The residue is chromatographed on a column of 120 g of silica gel which is eluted with a mixture of chloroform and methanol (95:5). The eluate is evaporated with the aid of a rotary evaporator and the residue is recrystallized from toluene. Colourless crystals of 1-[5-(2-butyramido-ethyl)-2-thienylsulphonyl]-2-imino-3-cyclohexyl-imidazolidine of melting point 121°-125°C are obtained.

Workup

  1. customrises to 33°C
  2. customthe acetone is then evaporated off with the aid of a rotary evaporator
  3. extractionThe oil-water mixture which remains is extracted twice with 30 ml of ethyl acetate at a time
  4. washThe extracts are washed with 20 ml of saturated sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo
  7. customThe residue is chromatographed on a column of 120 g of silica gel which
  8. washis eluted with a mixture of chloroform and methanol (95:5)
  9. customThe eluate is evaporated with the aid of a rotary evaporator
  10. customthe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-686288313d4b4f349e472e9abcf27a55
Source dataset
uspto-grants-1976_03
Patent number
US03941804

Reaction notes

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