Methanol → Methyl 2-chloro-3-(oxazol-5-yl)-4-methylsulfonylbenzoate

HRID 355648Notes

Reaction equation

HRID 355648 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=[O:13])=[C:10]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].S([CH:28]([N+]#[C-])[N+:29]#[C-:30])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].CO>C(OCC)(=O)C>[Cl:1][C:2]1[C:11]([C:12]2[O:13][CH:30]=[N:29][CH:28]=2)=[C:10]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 18517410Methyl 2-chloro-3-formyl-4-methylsulfonylbenzoateHCID 22123546Tosylmethylene isocyanide

Product 1

HCID 22123538Methyl 2-chloro-3-(oxazol-5-yl)-4-methylsulfonylbenzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

25 g (0.09 mol) of methyl 2-chloro-3-formyl-4-methylsulfonylbenzoate (Ex. A.1.), 17.6 g (0.09 mol) of tosylmethylene isocyanide and 6.2 g (0.045 mol) of finely pulverulent potassium carbonate are stirred together with 450 ml of methanol at reflux temperature for 5 hours. The solvent was subsequently stripped off, the residue was taken up in ethyl acetate, and the mixture was extracted with water. The ethyl acetate phase was dried using sodium sulfate and concentrated.

Workup

  1. temperatureat reflux temperature for 5 hours
  2. extractionthe mixture was extracted with water
  3. dry with materialThe ethyl acetate phase was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1aee90bfe9e84a8a8b404394690a88ca
Source dataset
uspto-grants-1998_11
Patent number
US05834402

Reaction notes

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