Isoamyl Nitrite → Methyl 3-(3-trifluoromethylphenyl)-5-isothiazolecarboxylate

HRID 67648Notes

Reaction equation

HRID 67648 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:9]2[C:13](N)=[C:12]([C:15]([O:17][CH3:18])=[O:16])[S:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1.N(OCCC(C)C)=O>O1CCCC1>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[C:5]([C:9]2[CH:13]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[S:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 13073199Methyl 4-amino-3-[3-(trifluoromethyl)phenyl]-1,2-thiazole-5-carboxylate

Product 1

HCID 13073224Methyl 3-(3-trifluoromethylphenyl)-5-isothiazolecarboxylateYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.5 g. of methyl 3-(3-trifluoromethylphenyl)-4-amino-5-isothiazolecarboxylate and 5.1 g. of isoamyl nitrite in 50 ml. of tetrahydrofuran was heated to reflux for one-half hour. The reaction mixture then was cooled, and the solvent was removed by evaporation under reduced pressure to provide a solid product which was crystallized from ethanol and water to give 2.8 g. (66% yield) of methyl 3-(3-trifluoromethylphenyl)-5-isothiazolecarboxylate. M.P. 82°-83° C.

Workup

  1. temperatureto reflux for one-half hour
  2. temperatureThe reaction mixture then was cooled
  3. customthe solvent was removed by evaporation under reduced pressure
  4. customto provide a solid product which
  5. customwas crystallized from ethanol and water
  6. customto give 2.8 g

Sources & evidence

ORD record
ord-c94d56be7c114e85a3dd00bee63810c7
Source dataset
uspto-grants-1982_08
Patent number
US04346094

Reaction notes

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