Sodium Hydroxide → HCID 178464624, compound

HRID 463771Notes

Reaction equation

HRID 463771 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+].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](Cl)=[O:30])=[CH:24][CH:23]=1>CC(C)=O>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([NH:13][C:11]([NH:10][CH2:8][CH3:9])=[NH:12])=[O:30])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 906924-Chlorophenylacetyl chlorideHCID 178464632HCID 178464632, compound

Product 1

HCID 178464624HCID 178464624, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of a 50% aqueous solution of sodium hydroxide (8.80 g), ethylguanidine sulfate (14.98 g), and 100 ml of acetone is stirred for 21/2 hrs at RT. The reaction mixture is treated with anhydrous sodium sulfate (6.0 g) and stirred for 1 hr. A solution of 4-chlorophenylacetylchloride (9.45 g) in 50 ml acetone is added to the reaction mixture dropwise and the mixture stirred overnight. The mixture is filtered, and the filtrate diluted with 100 ml of saturated aqueous sodium bicarbonate and the acetone evaporated in vacuo. The aqueous mixture 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 evaporated in vacuo. The resulting solution is treated with ethereal hydrochloric acid, and the solvent evaporated in vacuo. The residue is stirred with 200 ml of diethyl ether for 1/2 hr. The diethyl-ether insoluble solid is collected and dried in air. The product is recrystallized from CH3CN to afford 6.03 g of white crystalline solid, M.P. 146°-147° C.

Workup

  1. stirringstirred for 1 hr
  2. stirringthe mixture stirred overnight
  3. filtrationThe mixture is filtered
  4. additionthe filtrate diluted with 100 ml of saturated aqueous sodium bicarbonate
  5. customthe acetone evaporated in vacuo
  6. additionThe aqueous mixture is diluted with 100 ml of H2O
  7. extractionextracted with two 100 ml portions of methylene chloride
  8. dry with materialThe combined extracts are dried with sodium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. additionThe resulting solution is treated with ethereal hydrochloric acid
  12. customthe solvent evaporated in vacuo
  13. stirringThe residue is stirred with 200 ml of diethyl ether for 1/2 hr
  14. customThe diethyl-ether insoluble solid is collected
  15. customdried in air
  16. customThe product is recrystallized from CH3CN

Sources & evidence

ORD record
ord-c5be0ed1c0d345249f2da622a7caaf6b
Source dataset
uspto-grants-1985_10
Patent number
US04544670

Reaction notes

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