Nitronium tetrafluoroborate → HCID 19965157, compound

HRID 977106Notes

Reaction equation

HRID 977106 reaction equation
N[C:2]1[CH:3]=[C:4]([C:13]2[S:14][C:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:16]([CH3:18])[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]([CH3:12])[CH3:11].[F:24][B-](F)(F)F.O=[N+]=O>C(Cl)Cl>[F:24][C:2]1[CH:3]=[C:4]([C:13]2[S:14][C:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:16]([CH3:18])[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 11073463Nitronium tetrafluoroborateHCID 19965080Ethyl 2-[3-amino-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 19965157HCID 19965157, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

330 mg of Ethyl 2-(3-amino-4-isobutyloxyphenyl)-4-methyl-5-thiazolecarboxylate was dissolved in 15 ml of methylene chloride, 130 mg of nitronium tetrafluoroborate was added thereto with ice cooling, followed by stirring for 4 hours. The reaction mixture was concentrated, irradiated with a UV lamp at 300 nm for 20 hours and purified by silica gel chromatography to give 175 mg of ethyl 2-(3-fluoro-4-isobutyloxyphenyl)-4-methyl-5-thiazolecarboxylate. This product was hydrolyzed by a conventional process and recrystallized from acetone-water to give 108 mg of 2-(3-fluoro-4-isobutyloxyphenyl)-4-methyl-5-thiazolecarboxylic acid (yield: 35%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customirradiated with a UV lamp at 300 nm for 20 hours
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-d9b539c052fe4d4c9a068d1fd552ce89
Source dataset
uspto-grants-1997_03
Patent number
US05614520

Reaction notes

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