1-Chloro-4-(chloromethyl)benzene → HCID 25142816, compound

HRID 275324Notes

Reaction equation

HRID 275324 reaction equation
[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[N:4]2[C@H:12]3[CH2:17][CH2:16][CH2:15][C@H:13]3[N:14]=[C:3]12.[H-].[Na+].[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1>CN(C=O)C>[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[N:8]([CH2:25][C:24]3[CH:27]=[CH:28][C:21]([Cl:20])=[CH:22][CH:23]=3)[CH:7]=[N:6][C:5]=2[N:4]2[C@H:12]3[CH2:17][CH2:16][CH2:15][C@H:13]3[N:14]=[C:3]12

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 10657146HCID 10657146, compound

Product 1

HCID 25142816HCID 25142816, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
50 °C

Procedure

Add a solution of cis-5,6a,7,8,9,9a-hexahydro-5-methylcyclopenta[4,5]imidazo[2,1-b]purin-4-one (0.5 g=2.2 mmol)in DMF drop-wise to a slurry of 60% NaH (0.1 g=2.4 mmol) in DMF at 30° C. When gas evolution ceases, add 4-chlorobenzyl chloride (0.5 g=2.4 mmol) in 2 ml DMF. Heat at 50° C. two hours. Remove DMF and partition between EtOAc and water. Dry, solvent strip, and recrystallize from CH3CN to give the title compound, a white solid. CI MS: M+ =356.

Workup

  1. customRemove DMF and partition between EtOAc and water
  2. customDry
  3. customsolvent strip, and recrystallize from CH3CN

Sources & evidence

ORD record
ord-4bdc1493d6ae4e0a810f61d2ace0c806
Source dataset
uspto-grants-1995_02
Patent number
US05393755

Reaction notes

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