Benzyl Chloride → HCID 18975412, compound

HRID 2393391Notes

Reaction equation

HRID 2393391 reaction equation
C([NH:4][CH:5]1[C:17]2[N:16]3[CH:18]=[CH:19][N:20]=[C:15]3[C:14](=[O:21])[NH:13][C:12]=2[C:11]2[CH:10]=[C:9]([Cl:22])[CH:8]=[CH:7][C:6]1=2)(=[O:3])C.[H-].[Na+].[CH2:25](Cl)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CS(C)=O.Cl>[OH2:3].[OH2:3].[NH2:4][C:5]1([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:17]2[N:16]3[CH:18]=[CH:19][N:20]=[C:15]3[C:14](=[O:21])[NH:13][C:12]=2[C:11]2[CH:10]=[C:9]([Cl:22])[CH:8]=[CH:7][C:6]1=2

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 18975453HCID 18975453, compound

Product 1

HCID 18975412HCID 18975412, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 679Dimethyl SulfoxideSolvent

Procedure

To 2 g of 10-acetamido-7-chloro-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one in 40 ml of anhydrous dimethyl sulphoxide, maintained at 20° C. under a nitrogen atmosphere, is added 0.61 g of 60% sodium hydride and the mixture is stirred for 90 minutes. 0.8 ml of benzyl chloride are then added dropwise and the stirring is continued for 24 hours. The reaction medium is then poured onto 50 ml of ice-water, then acidified using 1N hydrochloric acid (12 ml). The precipitate formed is filtered off, washed with water and then with acetone, and dried. The crude product thus obtained (1.8 g) is taken up in 20 ml of 6N hydrochloric acid and maintained at reflux for 2 hours. The insoluble product is filtered off, washed with water and recrystallized from 45 ml of a mixture of ethanol and water (1/2 by volume) to give 0.31 g of 10-amino-10-benzyl-7-chloro-5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-one dihydrate in the form of a white powder melting at 241° C. (Analysis, C20H19ClN4O3.0.82 HCl, % calculated C: 60.23; H: 4.80;

Workup

  1. waitthe stirring is continued for 24 hours
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. washwashed with water
  5. dry with materialwith acetone, and dried
  6. customThe crude product thus obtained (1.8 g)
  7. temperaturemaintained
  8. temperatureat reflux for 2 hours
  9. filtrationThe insoluble product is filtered off
  10. washwashed with water
  11. customrecrystallized from 45 ml of a mixture of ethanol and water (1/2 by volume)

Sources & evidence

ORD record
ord-6b7c50bdf5744c36b299a573ee0894b8
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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