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Acetic Anhydride → 4-((6-Acetylmethylamino-3-pyridinyl)methylene)-2-(2-thienyl)-5(4H)-oxazolone

HRID 1474476
Notes
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Reaction equation

HRID 1474476 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=O.[CH3:13][NH:14][C:15]1[N:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][CH:16]=1.[C:23]([O-])(=[O:25])[CH3:24].[Na+].C(OC(=O)C)(=O)C>O>[C:23]([CH2:13][NH:14][C:15]1[N:20]=[CH:19][C:18]([CH:21]=[C:9]2[C:10](=[O:11])[O:12][C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[N:8]2)=[CH:17][CH:16]=1)(=[O:25])[CH3:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 679227((2-Thienylcarbonyl)amino)acetic acidHCID 184162986-(Methylamino)nicotinaldehyde

Product 1

HCID 866598544-((6-Acetylmethylamino-3-pyridinyl)methylene)-2-(2-thienyl)-5(4H)-oxazoloneYield 28.5%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
90 °C

Procedure

To a screw-capped test tube, N-(2-thienylcarbonyl)glycine (56 mg, 0.3 mmol), 6-(methylamino)-3-pyridinecarboxaldehyde (45 mg, 0.3 mmol), sodium acetate (25 mg, 0.3 mmol) and acetic anhydride (0.3 mL) were added. The test tube was sealed, and it was then stirred at an external temperature of 90° C. Three hours later, the temperature of the reaction solution was returned to room temperature, and water (1.5 mL) was then added thereto. The obtained mixture was stirred at the same temperature as described above for 1.5 hours. Thereafter, the precipitated crystal was collected by filtration, and it was washed with water (5 mL) and was then dried under reduced pressure, so as to obtain 28 mg of the above-captioned compound.

Workup

  1. customThe test tube was sealed
  2. customThree hours
  3. customwas returned to room temperature
  4. stirringThe obtained mixture was stirred at the same temperature
  5. customas described above for 1.5 hours
  6. filtrationThereafter, the precipitated crystal was collected by filtration, and it
  7. washwas washed with water (5 mL)
  8. customwas then dried under reduced pressure

Sources & evidence

ORD record
ord-7750f8f42ab240c491a05417df8ffa22
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09018238B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes