Hydrochloric Acid → HCID 178470658, compound

HRID 1976299Notes

Reaction equation

HRID 1976299 reaction equation
Cl.[C:2]([NH2:10])(=[NH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].[CH2:13]([O:15][C:16]([CH2:18][C:19]1([CH3:36])[CH2:28][CH2:27][C:26]2[C:21](=[C:22]([CH3:35])[C:23]([CH3:34])=[C:24]([S:30](Cl)(=[O:32])=[O:31])[C:25]=2[CH3:29])[O:20]1)=[O:17])[CH3:14].Cl>CC(C)=O.CCOC(C)=O.O>[CH2:13]([O:15][C:16]([CH2:18][C:19]1([CH3:36])[CH2:28][CH2:27][C:26]2[C:21](=[C:22]([CH3:35])[C:23]([CH3:34])=[C:24]([S:30]([NH:9][C:2](=[NH:10])[C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)(=[O:31])=[O:32])[C:25]=2[CH3:29])[O:20]1)=[O:17])[CH3:14]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 80289Benzamidine, hydrochlorideHCID 22000916HCID 22000916, compound

Product 1

HCID 178470658HCID 178470658, compoundYield 40.2%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of benzamidine hydrochloride (2.72 g) in acetone (70 ml) was added 1N aqueous sodium hydroxide (1N NaOH) (17.3 ml) under ice-cooling. To the mixture of a solution of 2-ethoxycarbonylmethyl-2,5,7,8-tetramethylchroman-6-sulfonyl chloride (3.25 g) in acetone (15 ml) was added dropwise over 15 minutes under ice-cooling, and stirred at room temperature for 20 hours. Acetone was removed under reduced pressure to give a residue. To the residue was added a mixture of water and AcOEt and the mixture was acidified with 1N HCl. The separated organic phase was washed with water and brine, and dried over MgSO4. After filtration, the filtrate was evaporated and purified by chromatography over silica gel (AcOEt-hexane 50:50 as eluent) to give N-(2-ethoxycarbonylmethyl-2,5,7,8-tetramethylchroman-6-sulfonyl)benzamidine as a glass (1.60 g).

Workup

  1. temperaturecooling
  2. additionwas added dropwise over 15 minutes under ice-
  3. temperaturecooling
  4. customAcetone was removed under reduced pressure
  5. customto give a residue
  6. additionTo the residue was added
  7. washThe separated organic phase was washed with water and brine
  8. dry with materialdried over MgSO4
  9. filtrationAfter filtration
  10. customthe filtrate was evaporated
  11. custompurified by chromatography over silica gel (AcOEt-hexane 50:50 as eluent)

Sources & evidence

ORD record
ord-437c5e8cdee44297af39bb67c85ac61a
Source dataset
uspto-grants-2001_05
Patent number
US06225480B1

Reaction notes

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