8-Chlorotheophylline → HCID 777316, compound

HRID 984826Notes

Reaction equation

HRID 984826 reaction equation
[Cl:1][C:2]1[NH:11][C:10]2[C:9](=[O:12])[N:7]([CH3:8])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=1.[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18]Cl>>[Cl:1][C:2]1[N:11]([CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[Cl:15])[C:10]2[C:9](=[O:12])[N:7]([CH3:8])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=1

Participants

3

Reactant 2

HCID 106618-ChlorotheophyllineHCID 119062-Chlorobenzyl chloride2×

Product 1

HCID 777316HCID 777316, compound

Procedure

From 8-Chorotheophylline (10 g, 47 mmol)) and 2-chlorobenzyl chloride (19.4 ml, 153.9 mmol). The 2-chlorobenzyl chloride was added in three portions. First third at reaction start as described in general procedure (E), and the other thirds after 24 and 48 hours respectively as the reaction had not completed. Total reaction time 7 days at RT. Due to incomplete precipitation in water the product was extracted with DCM (700 and 300 ml), dried (MgSO4), and evaporated to dryness in vacuo. Excess 2-chlorobenzyl bromide was removed by washing the product in Et2O.

Workup

  1. customFirst third at reaction start
  2. customafter 24 and 48 hours
  3. customTotal reaction time 7 days
  4. customat RT
  5. customDue to incomplete precipitation in water the product
  6. extractionwas extracted with DCM (700 and 300 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated to dryness in vacuo
  9. customExcess 2-chlorobenzyl bromide was removed
  10. washby washing the product in Et2O

Sources & evidence

ORD record
ord-c3306cb981754294b7ef2578bc231286
Source dataset
uspto-grants-2005_03
Patent number
US06869947B2

Reaction notes

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