Hydrochloric Acid → 2-{4-[2-(2-Nitrophenyl)-vinyl]-phenyl}-6-methoxybenzothiazole

HRID 339489Notes

Reaction equation

HRID 339489 reaction equation
[O:1]([C:3]1[CH:26]=[CH:25][C:6]2[N:7]=[C:8]([C:10]3[CH:24]=[CH:23][C:13]([CH2:14]P(=O)(OCC)OCC)=[CH:12][CH:11]=3)[S:9][C:5]=2[CH:4]=1)[CH3:2].[N+:27]([C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH:32]=O)([O-:29])=[O:28].C[O-].[Na+].Cl>CO.O>[N+:27]([C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH:32]=[CH:14][C:13]1[CH:12]=[CH:11][C:10]([C:8]2[S:9][C:5]3[CH:4]=[C:3]([O:1][CH3:2])[CH:26]=[CH:25][C:6]=3[N:7]=2)=[CH:24][CH:23]=1)([O-:29])=[O:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 111012-NitrobenzaldehydeHCID 10942334Sodium MethoxideHCID 13599215Diethyl 4-(6-methoxybenzothiazol-2-yl)benzylphosphonate

Product 1

HCID 672367122-{4-[2-(2-Nitrophenyl)-vinyl]-phenyl}-6-methoxybenzothiazoleYield 44.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of diethyl 4-(6-methoxylbenzothiazol-2-yl)benzylphosphonate (0.10 g, 0.25 mmol) and 2-nitrobenzaldehyde (0.39 g, 0.25 mmol) in dry MeOH (10 ml) at 0° C. was added dropwise a solution of 0.5 M sodium methoxide (1.02 ml, 0.51 mmol). The reaction mixture was then allowed to rise to room temperature and heated under reflux for 18 h. The reaction mixture was cooled to room temperature and water (30 ml) was added followed by 1 M HCl until the reaction mixture became acidic. The reaction mixture was then extracted with DCM (3×80 ml) and the combined organic extracts washed with brine (50 ml) and dried (Na2SO4). The solvent was removed under reduced pressure to give a solid which was purified by flash chromatography (DCM) to give the title compound (0.043 g, 43%) as a yellow solid.

Workup

  1. customto rise to room temperature
  2. temperatureheated
  3. temperatureunder reflux for 18 h
  4. extractionThe reaction mixture was then extracted with DCM (3×80 ml)
  5. washthe combined organic extracts washed with brine (50 ml)
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was removed under reduced pressure
  8. customto give a solid which
  9. customwas purified by flash chromatography (DCM)

Sources & evidence

ORD record
ord-bf730d2810124dec845a7553130dedc8
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

Loading…