Dimethylacetamide → HCID 18176007, compound

HRID 394444Notes

Reaction equation

HRID 394444 reaction equation
[CH3:1]C(N(C)C)=O.[NH2:7][C:8]1[C:9]([OH:27])=[C:10]([N:16]2[C:21](=[O:22])[N:20]([CH3:23])[C:19](=[S:24])[N:18]([CH3:25])[C:17]2=[O:26])[C:11]([F:15])=[CH:12][C:13]=1[Cl:14]>CO>[Cl:14][C:13]1[C:8]2[N:7]=[CH:1][O:27][C:9]=2[C:10]([N:16]2[C:21](=[O:22])[N:20]([CH3:23])[C:19](=[S:24])[N:18]([CH3:25])[C:17]2=[O:26])=[C:11]([F:15])[CH:12]=1

Participants

4

Reactant 2

HCID 31374DimethylacetamideHCID 18176015HCID 18176015, compound

Product 1

HCID 18176007HCID 18176007, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.0 g (48.1 mmol) of trimethylformamide were added dropwise to a solution of 502 mg (1.50 mmol) of 3-(3-amino-4-chloro-6-fluoro-2-hydroxyphenyl)-1,5-dimethyl-6-thioxo-[1,3,5]-triazinane-2,4-dione in 10 ml of methanol. The mixture was then heated at reflux temperature for 9 hours. The reaction mixture was subsequently concentrated under reduced pressure. The resulting crude product was purified by means of column chromatography (mobile phase: cyclohexane/ethyl acetate=20:1). Yield: 240 mg (46%); m.p.: 209-211° C.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux temperature for 9 hours
  3. concentrationThe reaction mixture was subsequently concentrated under reduced pressure
  4. customThe resulting crude product was purified by means of column chromatography (mobile phase: cyclohexane/ethyl acetate=20:1)

Sources & evidence

ORD record
ord-1d4e505e6bc744c9babe486604b1d023
Source dataset
uspto-grants-2003_08
Patent number
US06602825B1

Reaction notes

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