2-Acetamido-4-chloromethylthiazole → HCID 20491756, compound

HRID 434648Notes

Reaction equation

HRID 434648 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.[C:9]([NH:12][C:13]1[S:14][CH:15]=[C:16]([CH2:18]Cl)[N:17]=1)(=[O:11])[CH3:10]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CN(C)C=O>[C:9]([NH:12][C:13]1[S:14][CH:15]=[C:16]([CH2:18][N:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[N:6][C:5]2=[O:8])[N:17]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 2

HCID 819632-Acetamido-4-chloromethylthiazoleHCID 1085785-Chloro-2(1H)-pyrimidinone

Product 1

HCID 20491756HCID 20491756, compoundYield 11.9%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A stirred suspension of 5-chloropyrimidin-2-one (653 mg), 2-acetylamino-4-chloromethylthiazole (1.430 g) anhydrous sodium carbonate (1.060 g) and benzyltrimethylammonium chloride (20 mg) in dry N,N-dimethylformamide (25 ml) was heated at 90° C. After 11/2 h the reaction mixture was evaporated to dryness and then the residue was suspended in ethyl acetate (250 ml) and washed with water (3×70 ml), dried (MgSO4) and evaporated to a yellow foam. The foam was subjected to p.l.c. on silica developing with chloroform-ethanol, 19:1 (three runs). The major band was eluted with ethyl acetate to give a foam which was crystallised from acetone to give off white crystals of the title pyrimidinone (170 mg), m.p. 209°-211° C., λmax (EtOH) 227 nm (ε 11,960), 267 nm (ε 8,540), 334 nm (ε 3,420).

Workup

  1. customAfter 11/2 h the reaction mixture was evaporated to dryness
  2. washwashed with water (3×70 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated to a yellow foam
  5. washThe major band was eluted with ethyl acetate
  6. customto give a foam which
  7. customwas crystallised from acetone

Sources & evidence

ORD record
ord-3a9a83430c214c468b91a58d90329bcd
Source dataset
uspto-grants-1983_08
Patent number
US04399140

Reaction notes

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