Sodium hydride → Methyl 2-[2-(3-phenyl-1,2,4-thiadiazol-5-yloxy)-phenyl]-3-fluoromethoxy-acrylate

HRID 1250349Notes

Reaction equation

HRID 1250349 reaction equation
[C:1]1([C:7]2[N:11]=[C:10](S(C)(=O)=O)[S:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](=[CH:28][O:29][CH2:30][F:31])[C:24]([O:26][CH3:27])=[O:25].[H-].[Na+]>CN(C)C=O>[C:1]1([C:7]2[N:11]=[C:10]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23](=[CH:28][O:29][CH2:30][F:31])[C:24]([O:26][CH3:27])=[O:25])[S:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 50850675-(Methylsulfonyl)-3-phenyl-1,2,4-thiadiazoleHCID 54381247Methyl 2-(2-hydroxyphenyl)-3-fluoromethoxy-acrylate

Product 1

HCID 54483257Methyl 2-[2-(3-phenyl-1,2,4-thiadiazol-5-yloxy)-phenyl]-3-fluoromethoxy-acrylateYield 67.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3.2 g (0.005 mol) of 3-phenyl-5-methanesulphonyl-1,2,4-thiadiazole and 2.3 g of methyl 2-(2-hydroxyphenyl)-3-fluoromethoxy-acrylate in 10 ml of dry dimethylformamide is treated at 0° C. with 0.2 g (0.005 mol) of 80% strength sodium hydride in mineral oil. The mixture is stirred for 4 hours at this temperature, and for a further 18 hours without cooling, and then concentrated. The residue is taken up using ethyl acetate, the solution is washed with water, and the organic phase is dried over sodium sulphate and concentrated again. The crude product is chromatographed on silica gel using hexane/acetone (7:3). 1.3 g (67% of theory) of methyl 2-[2-(3-phenyl-1,2,4-thiadiazol-5-yloxy)-phenyl]-3-fluoromethoxy-acrylate are obtained as a yellow, highly viscous oil.

Workup

  1. temperaturefor a further 18 hours without cooling
  2. concentrationconcentrated
  3. washthe solution is washed with water
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. concentrationconcentrated again
  6. customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-6c4f4a7365c54a129967ce892acd254c
Source dataset
uspto-grants-2002_01
Patent number
US06337401B1

Reaction notes

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