Hydantoin → HCID 15116191, compound

HRID 703787Notes

Reaction equation

HRID 703787 reaction equation
[H-].[Na+].[NH:3]1[CH2:7][C:6](=[O:8])[NH:5][C:4]1=[O:9].Cl[CH2:11][C:12]([NH:14][C:15]1[C:16]2[C:21]([N:22]=[C:23]3[C:28]=1[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13].[Cl-].[NH4+]>CN(C)C=O>[NH:3]1[CH2:7][C:6](=[O:8])[N:5]([CH2:11][C:12]([NH:14][C:15]2[C:16]3[C:21]([N:22]=[C:23]4[C:28]=2[CH2:27][CH2:26][CH2:25][CH2:24]4)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[C:4]1=[O:9]

Participants

6

Reactant 4

HCID 10006HydantoinHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 144713012-Chloro-N-(1,2,3,4-tetrahydroacridin-9-yl)acetamide

Product 1

HCID 15116191HCID 15116191, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 20 ml of dimethylformamide was suspended 0.8 g (content: 60%) of sodium hydride, and then 3 g of 2,4-imidazolidinedione was added to the suspension and the mixture was stirred at room temperature for 30 minutes. Then, 2.75 g of 9-chloroacetylamino-1,2,3,4-tetrahydroacridine (described in "Chem. listy, Vol. 51, p. 1906 (1957)") was added to the mixture and reaction was carried out by heating to 80° C. for 30 minutes. After cooling to 10° C., the mixture was poured into 100 ml of an aqueous solution containing 8 g of ammonium chloride. Precipitated crystals were collected by filtration, washed with water and dried. These crystals were recrystallized from methanol-chloroform to give 2.5 g of the title compound. Melting point: 302° to 304° C. (decomposed).

Workup

  1. temperatureby heating to 80° C. for 30 minutes
  2. temperatureAfter cooling to 10° C.
  3. customPrecipitated crystals
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. customdried
  7. customThese crystals were recrystallized from methanol-chloroform

Sources & evidence

ORD record
ord-e66c2877938f4f2096c6d2f8de351bc2
Source dataset
uspto-grants-1991_01
Patent number
US04985430

Reaction notes

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