8-Chlorotheophylline → HCID 777316, compound

HRID 458629Notes

Reaction equation

HRID 458629 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-b3c0c1f82082457991d2d5088dd210f2
Source dataset
uspto-grants-2007_03
Patent number
US07192952B2

Reaction notes

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