Hydrochloric Acid → HCID 12766300, compound

HRID 1155512Notes

Reaction equation

HRID 1155512 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]([S:22][C:23]3C=CC([N+]([O-])=O)=CC=3[N+]([O-])=O)=[CH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.CI.[OH-].[K+].Cl>N#N.O.CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]([S:22][CH3:23])=[CH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodide2×HCID 14797Potassium HydroxideHCID 20561020HCID 20561020, compound

Product 1

HCID 12766300HCID 12766300, compoundYield 41.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 947NitrogenSolvent3×HCID 962WaterSolvent

Procedure

A suspension of 2,3-bis(4-methoxyphenyl)-5-(2,4-dinitrophenylthio)thiophene (4.8 g, 9.7 mmoles) in 20 ml N2 -purged methanol was cooled to 0° and treated with methyl iodide (1 ml, 14.6 mmoles) and a N2 -purged solution of potassium hydroxide (1.3 g, 19.4 mmoles) in a mixture of 5 ml water and 5 ml methanol. N2 -purged tetrahydrofuran (25 ml) was added and the reaction heated at reflux for 0.5 hour. An additional portion of methyl iodide (1 ml, 14.6 mmoles) was added and heating continued for 0.5 hour. The reaction mixture was cooled, poured into ≃50 ml 1 N HCl and extracted three times with ether and three times with ethyl acetate. The combined organic extracts were washed once with water, once with brine, dried and concentrated to a dark oil. Chromatography on silica gel and recrystallization from methanol gave the title compound (1.39 g), m.p. 106°-8°. Infrared and H-NMR spectra were consistent with the assigned structure. MS 342 (M+)

Workup

  1. temperaturewas cooled to 0°
  2. temperaturethe reaction heated
  3. temperatureat reflux for 0.5 hour
  4. temperatureheating
  5. temperatureThe reaction mixture was cooled
  6. extractionextracted three times with ether and three times with ethyl acetate
  7. washThe combined organic extracts were washed once with water, once with brine
  8. customdried
  9. concentrationconcentrated to a dark oil
  10. customChromatography on silica gel and recrystallization from methanol

Sources & evidence

ORD record
ord-b95e082f1b694c229565a4070e522ae7
Source dataset
uspto-grants-1981_11
Patent number
US04302461

Reaction notes

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