Sodium Hydroxide → HCID 178471705, compound

HRID 1976293Notes

Reaction equation

HRID 1976293 reaction equation
[OH-].[Na+].Cl.[C:4]([NH2:12])(=[NH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:13]([O:15][C:16]([CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([S:29](Cl)(=[O:31])=[O:30])=[C:24]([CH3:33])[C:23]=1[CH3:34])=[O:17])[CH3:14]>CC(C)=O>[CH2:13]([O:15][C:16]([CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([S:29]([NH:11][C:4](=[NH:12])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)(=[O:31])=[O:30])=[C:24]([CH3:33])[C:23]=1[CH3:34])=[O:17])[CH3:14]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 80289Benzamidine, hydrochlorideHCID 22000902HCID 22000902, compound

Product 1

HCID 178471705HCID 178471705, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

1N NaOH (6.43 ml) was added into a mixture of benzamidine hydrochloride (1.00 g) and acetone (25 ml) under ice-water cooling, and then a mixture of 4-(3-ethoxycarbonylpropoxy)-2,3,6-trimethylbenzenesulfonyl chloride (3.36 g) and acetone (5 ml) was added dropwise thereto over 10 minutes. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated by N2 flow to remove the excess of solvents, and was poured into a mixture of water and AcOEt. The separated organic phase was washed with sat. NaHCO3aq., water, and brine, and was dried over MgSO4. After evaporation, the resulting residue was purified by chromatography over silica gel (CHCl3-methanol (MeOH) as eluent) to give N-[4-(3-ethoxycarbonylpropoxy)-2,3,6-trimethylbenzenesulfonyl]benzamidine (1.39 g) as an oil compound.

Workup

  1. additionwas added dropwise
  2. concentrationThe reaction mixture was concentrated by N2 flow
  3. customto remove the excess of solvents
  4. additionwas poured into a mixture of water and AcOEt
  5. washThe separated organic phase was washed with sat. NaHCO3aq
  6. dry with material, water, and brine, and was dried over MgSO4
  7. customAfter evaporation
  8. customthe resulting residue was purified by chromatography over silica gel (CHCl3-methanol (MeOH) as eluent)

Sources & evidence

ORD record
ord-b84ffe3be4074bf18fb72cccc2bd7f94
Source dataset
uspto-grants-2001_05
Patent number
US06225480B1

Reaction notes

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