Sodium Hydroxide → HCID 178464625, compound

HRID 463774Notes

Reaction equation

HRID 463774 reaction equation
[OH-].[Na+].S(O)(O)(=O)=O.[CH2:8]([NH:10][C:11]([NH2:13])=[NH:12])[CH3:9].S([O-])([O-])(=O)=O.[Na+].[Na+].[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:29][C:30](Cl)=[O:31])[CH:26]=[CH:27][CH:28]=1>CC(C)=O>[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:29][C:30]([NH:13][C:11]([NH:10][CH2:8][CH3:9])=[NH:12])=[O:31])[CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 27332463-Methoxyphenylacetyl chlorideHCID 178464632HCID 178464632, compound

Product 1

HCID 178464625HCID 178464625, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

8.80 g of a 50% aqueous sodium hydroxide solution, ethylguanidine sulfate (14.98 g), and 100 ml of acetone are stirred for 21/2 hrs at RT. The resulting mixture is treated with anhydrous sodium sulfate (6.0 g) and stirring continued for 1 hr. A solution of 3-methoxyphenylacetyl chloride (9.23 g) in 50 ml acetone is added to the mixture dropwise and the reaction mixture stirred overnight at RT. The mixture is filtered and the filtrate diluted with saturated aqueous sodium bicarbonate. The acetone is evaporated in vacuo. The aqueous residue is diluted with 100 ml of H2O and extracted with two 100 ml portions of methylene chloride. The combined extracts are dried with sodium sulfate, filtered and concentrated in vacuo. The resulting solution is acidified with ethereal hydrochloric acid and the solvent evaporated in vacuo. The residue is stirred with 200 ml of diethyl ether and the solid collected, washed with diethyl ether and recrystallized from acetone, affording the product, M.P. 108°-110° C.

Workup

  1. stirringthe reaction mixture stirred overnight at RT
  2. filtrationThe mixture is filtered
  3. additionthe filtrate diluted with saturated aqueous sodium bicarbonate
  4. customThe acetone is evaporated in vacuo
  5. additionThe aqueous residue is diluted with 100 ml of H2O
  6. extractionextracted with two 100 ml portions of methylene chloride
  7. dry with materialThe combined extracts are dried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customthe solvent evaporated in vacuo
  11. stirringThe residue is stirred with 200 ml of diethyl ether
  12. customthe solid collected
  13. washwashed with diethyl ether
  14. customrecrystallized from acetone
  15. customaffording the product, M.P. 108°-110° C.

Sources & evidence

ORD record
ord-b550016ed6ea458dbeb4716a44f47dcc
Source dataset
uspto-grants-1985_10
Patent number
US04544670

Reaction notes

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