Hydrochloric Acid → 3-(Amino-benzoyl)thiophene

HRID 2231749

Reaction equation

HRID 2231749 reaction equation
C1(C([C:8]2[CH:9]=[C:10]([NH:14]C(C3C=CN4C=3CSC4C3C=NC=CC=3)=O)[CH:11]=[CH:12][CH:13]=2)=O)SC=CC=1.[C:31]1(C(C2C=C([N+]([O-])=O)C=CC=2)=O)[S:35][CH:34]=[CH:33]C=1.Cl.[OH-].[Na+].[CH2:50]([OH:52])[CH3:51]>C(OCC)C.O>[CH:31]1[S:35][CH:34]=[CH:33][C:51]=1[C:50]([C:11]1[CH:12]=[CH:13][CH:8]=[CH:9][C:10]=1[NH2:14])=[O:52]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 348407(3-Nitrophenyl)-thiophen-2-ylmethanoneHCID 21285566N-[3-(2-thenoyl)phenyl]-3-(3-pyridyl)1H,3H-pyrrolo[1,2-c]thiazole-7-carboxamide

Product 1

HCID 127505413-(Amino-benzoyl)thiophene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
4 °C

Procedure

The 3-(2-thenoyl)aniline may be prepared as follows: Stannous chloride in the dihydrate form (22.8 g) is added, at a temperature in the vicinity of 4° C., to a suspension of 3-(2-thenoyl)nitrobenzene (6.8 g) in a 3.7N solution (130 cc) of hydrogen chloride in ethanol, in the course of 40 minutes. After stirring at a temperature in the vicinity of 4° C. for 1 hour and then at a temperature in the vicinity of 20° C. for 1 hour, the solution obtained is heated at a temperature in the vicinity of 78° C. for 1 hour. The solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 50° C. The residue obtained is taken up with a mixture of distilled water (50 cc) and diethyl ether (100 cc), to which an aqueous 10N sodium hydroxide solution (130 cc) is added at a temperature in the vicinity of 15° C. The organic phase is separated and the aqueous phase is extracted 4 times with diethyl ether (400 cc in total). The ether extracts are combined, washed 3 times with distilled water (300 cc in total), dried over anhydrous magnesium sulphate, treated with decolourizing charcoal (0.5 g), and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 40° C. 2-(3-Thenoyl)aniline (5.7 g) in the form of yellow crystals m.p. 105° C., is thereby obtained.

Workup

  1. waitat a temperature in the vicinity of 20° C. for 1 hour
  2. customthe solution obtained
  3. temperatureis heated at a temperature in the vicinity of 78° C. for 1 hour
  4. customThe solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 50° C
  5. customThe residue obtained
  6. additionis added at a temperature in the vicinity of 15° C
  7. customThe organic phase is separated
  8. extractionthe aqueous phase is extracted 4 times with diethyl ether (400 cc in total)
  9. washwashed 3 times with distilled water (300 cc in total)
  10. dry with materialdried over anhydrous magnesium sulphate
  11. additiontreated with decolourizing charcoal (0.5 g)
  12. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 40° C

Sources & evidence

ORD record
ord-4a026a1829e94386a97cc33d6573d67f
Source dataset
uspto-grants-1988_11
Patent number
US04783472

Linked notes

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