Acetic Anhydride → HCID 75238407, compound

HRID 1474471Notes

Reaction equation

[CH3:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]([OH:13])=[O:12])=O)=[CH:4][CH:3]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:22]=O)[CH:19]=[N:20][CH:21]=1.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>O>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:10]2[C:11](=[O:12])[O:13][C:7]([C:5]3[S:6][C:2]([CH3:1])=[CH:3][CH:4]=3)=[N:9]2)[CH:19]=[N:20][CH:21]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a screw-capped test tube, N-[(5-methyl-2-thienyl)carbonyl]glycine (60 mg, 0.3 mmol), 5-methoxy-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 51 mg of the above-captioned compound.

Workup

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

Sources & evidence

ORD record: ord-86496ae4e8ff44d49d25f1521b9c62d5
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018238B2

Reaction notes

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