Phenacyl bromide → HCID 20475753, compound

HRID 905217Notes

Reaction equation

HRID 905217 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](=[S:8])[NH:6][CH:7]=1.C(N(CC)CC)C.[CH2:16](Br)[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18]>CCO>[CH2:16]([S:8][C:5]1[N:6]=[CH:7][C:2]([Br:1])=[CH:3][N:4]=1)[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 8471TriethylamineHCID 146218495-Bromopyrimidine-2(1H)-thione

Product 1

HCID 20475753HCID 20475753, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Bromopyrimidine-2-thione (10.5 mmol) was added to a solution of triethylamine (11.6 mmol) in EtOH (130 ml) and the mixture stirred for 15 min before addition of phenacyl bromide (10.5 mmol). The reaction mixture was stirred for 1 h before the solvent was removed at reduced pressure, the residue extracted with chloroform and the chloroform solution chromatographed on alumina (100 g, activity I); yield 71%, m.p. 107°-109° C. (iPrOH). 1H NMR (CDCl3): δ4.60 (CH2), 7.5-8.0 (Ph), 8.46 (H-4, H-6).

Workup

  1. customwas removed at reduced pressure
  2. extractionthe residue extracted with chloroform
  3. customthe chloroform solution chromatographed on alumina (100 g, activity I)

Sources & evidence

ORD record
ord-75f6a88457eb4a7cb715cd141b51bf36
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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