1-Methylimidazole → 3-{2-Chloro-6-(4,6-dimethoxypyrimidin-2-yl)oxybenzoyl}amino-2-oxazolidinone

HRID 846018Notes

Reaction equation

HRID 846018 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[N:13]=2)[C:3]=1[C:4]([OH:6])=O.S(O)(O)(=O)=O.[NH2:27][N:28]1[CH2:32][CH2:31][O:30][C:29]1=[O:33].C(C1C=C(C(C)C)C=C(C(C)C)C=1S(Cl)(=O)=O)(C)C.CN1C=CN=C1>CN(C)C=O.O.C(N(CC)CC)C>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[N:13]=2)[C:3]=1[C:4]([NH:27][N:28]1[CH2:32][CH2:31][O:30][C:29]1=[O:33])=[O:6]

Participants

8

Reactant 4

HCID 13901-MethylimidazoleHCID 810422,4,6-Tris(1-methylethyl)benzenesulfonyl chlorideHCID 12228384N-amino-1,3-oxazolidin-2-one sulphateHCID 156119442-Chloro-6-((4,6-dimethoxypyrimidin-2-yl)oxy)benzoic acid

Product 1

HCID 198844333-{2-Chloro-6-(4,6-dimethoxypyrimidin-2-yl)oxybenzoyl}amino-2-oxazolidinone

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

1.24 Grams of 2-chloro-6-(4,6-dimethoxypyrimidin-2-yl)oxybenzoic acid was dissolved in 20 ml of N,N-dimethylformamide. To the solution were added 1.20 g of 3-amino-2-oxazolidinone sulfate, 0.67 g of triethylamine, 1.82 g of 2,4,6-triisopropylbenzenesulfonyl chloride and 0.98 g of 1-methylimidazole. The resulting solution was stirred at room temperature for 3 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer separated therefrom was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed from the dried layer under reduced pressure to obtain a residue. Purifying the residue with thin layer chromatography (silica gel, chloroform/methanol: 9/1 by volume) gave 0.2 g of 3-{2-chloro-6-(4,6-dimethoxypyrimidin-2-yl)oxybenzoyl}amino-2-oxazolidinone (present compound (172)).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer separated
  3. washtherefrom was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed from the dried layer under reduced pressure
  6. customto obtain a residue
  7. customPurifying the residue with thin layer chromatography (silica gel, chloroform/methanol: 9/1 by volume)

Sources & evidence

ORD record
ord-07a37fbf9f714142ae2458cbbf31f6ff
Source dataset
uspto-grants-1992_08
Patent number
US05135563

Reaction notes

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