Benzoyl chloride → HCID 5073926, compound

HRID 2217326Notes

Reaction equation

I.[S:2]1[C:6]2[CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:5]=2[N:4]=[C:3]1[NH2:14].[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N1C=CC=CC=1>[S:2]1[C:6]2[CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:5]=2[N:4]=[C:3]1[NH:14][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of Indeno[1,2-d]thiazol-2-ylamine hydroiodide 1a (100 mg; 0.32 mmol) in pyridine (2 mL) was added benzoyl chloride (0.12 mL; 0.96 mmol) dropwise. The mixture was then agitated at 80° C. in a sealed tube overnight. The mixture was allowed to cool to room temperature and the solvent removed in vacuo. The residue was taken up into ethyl acetate and the extract allowed to stir with 2M sodium carbonate solution for 2 hours at room temperature. The organic layer was then washed with brine solution, dried over sodium sulfate and concentrated in vacuo. The crude product was chromatographed on silica gel (eluent: 10% ethyl acetate/hexanes to 40% ethyl acetate gradient) to provide 53 mg of N-(8H-Indeno[1,2-d]thiazol-2-yl)-benzamide 2. EI-HRMS m/e calcd for C17H12N2OS 292.0670, found 292.0666.

Workup

temperatureto cool to room temperature
customthe solvent removed in vacuo
stirringto stir with 2M sodium carbonate solution for 2 hours at room temperature
washThe organic layer was then washed with brine solution
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe crude product was chromatographed on silica gel (eluent: 10% ethyl acetate/hexanes to 40% ethyl acetate gradient)

Sources & evidence

ORD record: ord-271011d1bfc34483899205deb4f6ce5a
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07407977B2

Reaction notes

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