Acetic Anhydride → 4-Methylthio-5-bromo-6-methylpyrimid-2-one

HRID 1075173Notes

Reaction equation

HRID 1075173 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[C:7]([CH3:9])[NH:6][C:5](=[O:10])[N:4]=1.C(OC(=O)C)(=O)C.[Br:18]N1C(=O)CCC1=O.S(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH3:1][S:2][C:3]1[C:8]([Br:18])=[C:7]([CH3:9])[NH:6][C:5](=[O:10])[N:4]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 67184N-bromobutanimideHCID 8169462-Hydroxy-4-methyl-6-(methylthio)pyrimidineHCID 23665763Sodium Bisulfite

Product 1

HCID 204942884-Methylthio-5-bromo-6-methylpyrimid-2-oneYield 35%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Methylthio-6-methylpyrimid-2-one (see Wheeler, L. H. and MacFarland, F. D. J. Amer. Chem. Soc. 42 (1909) (43) (0.01 mol) was dissolved in acetic acid (30 ml) containing 2% acetic anhydride and N-bromo-succinimide (0.013 mol) added. The reaction mixture was kept at 55° C. for 40 min. Ice-cold water (150 ml) containing a little sodium bisulphite was added to the cold reaction mixture. The precipitate formed was recrystallised from water; yield 35%, m.p. 244° C. (Found: C, 30.34; H, 2.81. Calc. for C6H7BrN2OS: C, 30.65; H, 3.00).

Workup

  1. additionadded
  2. additionwas added to the cold reaction mixture
  3. customThe precipitate formed
  4. customwas recrystallised from water

Sources & evidence

ORD record
ord-20e2583cc65341feaeb3978879c6d5fa
Source dataset
uspto-grants-1983_07
Patent number
US04395406

Reaction notes

Loading…