Acetic Anhydride → HCID 178503572, compound

HRID 1075164Notes

Reaction equation

HRID 1075164 reaction equation
CSC1C=CNC(=O)N=1.[CH3:10][S:11][C:12]1[C:17]([Br:18])=[C:16](C)[NH:15][C:14](=[O:20])[N:13]=1.C(OC(=O)C)(=O)C.BrN1C(=O)CCC1=O.S(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH3:10][S:11][C:12]1[C:17]([Br:18])=[CH:16][NH:15][C:14](=[O:20])[N:13]=1

Participants

7

Reactant 5

HCID 7918Acetic AnhydrideHCID 67184N-bromobutanimideHCID 204942884-Methylthio-5-bromo-6-methylpyrimid-2-oneHCID 23665763Sodium BisulfiteHCID 178503296HCID 178503296, compound

Product 1

HCID 178503572HCID 178503572, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Methylthiopyrimid-2-one (prepared as described in Wheller, L. H. and Johnson, B. T. J. Amer. Chem. Soc. 42 (1909) (30), (0.01 mol) was dissolved at ca. 80° C. in acetic acid (30 ml) containing 2% acetic anhydride. The temperature was lowered to ca. 55° C. and N-bromosuccinimide (0.013 mol) added and the reaction mixture stirred at this temperature for 40 min. Ice-cold water (150 ml) containing a little sodium bisulphite was then added and the precipitated collected and recrystallised from water; yield 28%, m.p. 260° C.;

Workup

  1. customwas lowered to ca. 55° C.
  2. additionwas then added
  3. customthe precipitated collected
  4. customrecrystallised from water

Sources & evidence

ORD record
ord-bc817db23ba34f979a11c43532a729f9
Source dataset
uspto-grants-1983_07
Patent number
US04395406

Reaction notes

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