Benzenesulfonic Acid → HCID 66574443, compound

HRID 1424750Notes

Reaction equation

HRID 1424750 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:5][CH:4]=1.[C:19]1([S:25]([OH:28])(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1CCCCC1>C(OCC)(=O)C.CO>[C:19]1([S:25]([OH:28])(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7371Benzenesulfonic AcidHCID 8078CyclohexaneHCID 82148Agomelatine

Product 1

HCID 66574443HCID 66574443, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2 °C

Procedure

1 g of N-[2-(7-methoxy-1-naphthyl)ethyl]acetamide was dissolved in 15 ml ethyl acetate at room temperature and a solution of 0.78 g of benzenesulfonic acid in 1 ml of methanol was added. The immediate formation of small crystals was observed, the solution was cooled to 2° C. and 5 ml of cyclohexane was added as an antisolvent to improve the yield. The crystalline product (slightly brown tabular crystals) was isolated by filtration. The isolated solid gave the XRPD pattern shown in shown in FIG. 5, the DSC thermograph shown in FIG. 6 with an onset of melting of approximately 128.5° C. and the Raman spectrum shown in FIG. 7.

Workup

  1. customThe crystalline product (slightly brown tabular crystals) was isolated by filtration
  2. customThe isolated solid gave the XRPD pattern
  3. customof melting of approximately 128.5° C.

Sources & evidence

ORD record
ord-6ddcee9065eb458796656e5736a0157f
Source dataset
uspto-grants-2015_01
Patent number
US08927771B2

Reaction notes

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