Bromoacetyl bromide → HCID 135738551, compound

HRID 1532124Notes

Reaction equation

HRID 1532124 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[CH2:5]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[NH:15][C:16](=[O:26])[C:17]2[CH:22]=[N:21][N:20]([CH2:23][CH2:24][CH3:25])[C:18]=2[N:19]=1)[CH3:6].[Br:27][CH2:28][C:29](Br)=[O:30]>ClCCl>[Br:27][CH2:28][C:29]([C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:5][CH3:6])=[C:9]([C:14]2[NH:15][C:16](=[O:26])[C:17]3[CH:22]=[N:21][N:20]([CH2:23][CH2:24][CH3:25])[C:18]=3[N:19]=2)[CH:10]=1)=[O:30]

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) ChlorideHCID 135738567HCID 135738567, compound

Product 1

HCID 135738551HCID 135738551, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminum trichloride (1.34 g, 0.010 mol) was added portionwise to a stirred solution of 6-(2-ethoxyphenyl)-1-n-propyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (Example 13; 1.0 g, 0.0034 mol) and bromoacetyl bromide (1.35, 0.0067 mol) in dichloromethane (30 ml) at 0° C. The reaction solution was allowed to warm to room temperature, stirred for 14 hours, then for a further 2 hours under reflux. The cool reaction mixture was added dropwise to ice/water (50 g) and the resulting mixture stirred for 1 hour. The organic phase was separated and the aqueous phase extracted with dichloromethane (2×50 ml); the combined organic solutions were then washed with brine (10 ml) and dried (Na2SO4). Removal of the solvent by evaporation under vacuum gave an off-white solid which, when triturated with ether (20 ml) and dried, afforded the product as a white solid (1.29 g, 92%). A sample crystallised from ethyl acetate-hexane as colourless crystals, m.p. 164-166° C. Found: C, 51.88; H, 4.56; N, 13.13. C18H19BrN4O3 requires C, 51.56; H, 4.57; N, 13.36%.

Workup

  1. temperaturefor a further 2 hours under reflux
  2. customThe cool reaction mixture
  3. stirringthe resulting mixture stirred for 1 hour
  4. customThe organic phase was separated
  5. extractionthe aqueous phase extracted with dichloromethane (2×50 ml)
  6. washthe combined organic solutions were then washed with brine (10 ml)
  7. dry with materialdried (Na2SO4)
  8. customRemoval of the solvent
  9. customby evaporation under vacuum
  10. customgave an off-white solid which, when
  11. customtriturated with ether (20 ml)
  12. customdried

Sources & evidence

ORD record
ord-d2d50b9b072b4185bfd62cbb14c98088
Source dataset
uspto-grants-2001_03
Patent number
US06200980B1

Reaction notes

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