Phenacyl bromide → HCID 19833369, compound

HRID 2051364Notes

Reaction equation

HRID 2051364 reaction equation
[NH:1]1[C:10](=[S:11])[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[N:4]=[C:2]1[NH2:3].[CH2:12](Br)[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14].[C:22](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:3][C:2]1[N:4]=[C:5]2[C:9]([NH:8][CH:7]=[N:6]2)=[C:10]([S:11][CH2:22][CH2:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:14])[N:1]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 178508250HCID 178508250, compound

Product 1

HCID 19833369HCID 19833369, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of thioguanine (8.36 g), phenacyl bromide (9.95 g) and potassium carbonate (7.60 g) in N,N-dimethylformamide (100 cm3) was stirred at ambient temperature for 20 hours. The reaction mixture was filtered and the filtrate evaporated to give a cream solid. Recrystallisation from boiling methanol (100 cm3) gave 10.3 g (72.2%) of the title compound m.p. 204°-205° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated
  3. customto give a cream solid
  4. customRecrystallisation

Sources & evidence

ORD record
ord-f4dc43a2c75d4b8fa8694389b7b08ac8
Source dataset
uspto-grants-1991_05
Patent number
US05017701

Reaction notes

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