Sodium Hydroxide → 2-(3,4-Dimethoxyphenyl)-4-fluoro-1,3-benzothiazole

HRID 131621Notes

Reaction equation

HRID 131621 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[S:20])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1.[OH-].[Na+]>O.C(O)C.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[F:1][C:2]1[C:3]2[N:8]=[C:9]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=3)[S:20][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 11702019HCID 11702019, compound

Product 1

HCID 117019992-(3,4-Dimethoxyphenyl)-4-fluoro-1,3-benzothiazoleYield 55%

Reagents, catalysts & solvents 3

HCID 178511488HCID 178511488, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
95 °C

Procedure

A solution of N-(2-fluorophenyl)-3,4-dimethoxythiobenzamide (0.850 g, 2.92 mmol) and sodium hydroxide (0.93 g, 23.3 mmol) in water (10 mL) and ethanol (0.5 mL) was added dropwise to a solution of potassium ferricyanide (3.84 g, 11.7 mmol) in water (5 mL) at 95° C. The resulting solution was stirred at 95° C. for a further 2 h and then cooled in an ice bath. The precipitate was collected by vacuum filtration, washed with water and dissolved in ethyl acetate (10 mL) and insoluble material was removed by filtration. The filtrate was concentrated in vacuo and the crude product purified by column chromatography (dichloromethane) to give the required product as a pale yellow powder (0.46 g, 55% yield), mp 129° C.; 1H NMR (DMSO-d6) δ 7.95 (1H, m, ArH), 7.65 (2H, m, ArH), 7.42 (2H, m, ArH), 7.15 (1H, m, ArH), 3.90 (3H, s, OMe), 3.88 (3H, s, OMe); m/z (CI) 290 (M++1); Anal. (C15H12FNO2S) C, H, N. C: found 62.36%, calc. 62.27%; H: found 4.19%, calc.4.18%; N: found 4.93%, calc. 4.84%.

Workup

  1. temperaturecooled in an ice bath
  2. filtrationThe precipitate was collected by vacuum filtration
  3. washwashed with water
  4. dissolutiondissolved in ethyl acetate (10 mL)
  5. custominsoluble material was removed by filtration
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe crude product purified by column chromatography (dichloromethane)

Sources & evidence

ORD record
ord-4ad773408e8644349028421071ca49fb
Source dataset
uspto-grants-2008_06
Patent number
US07384966B2

Reaction notes

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