Hydrochloric Acid → HCID 67183833, compound

Temperature

2.5 °C

To a solution of methyl 3-amino-5-phenylthiophene-2-carboxylate (5 g, 21.4 mmol) and conc. HCl (9 mL, 85.8 mmol) in H2O (51 mL) was added acetone (30 mL) to dissolve the product. Then NaNO2 (1.7 g, 23.6 mmol) was added in portions for 15 min at 0° C. After stirring at 0-5° C. for 1 h, the reaction mixture was added to the solution of K2CO3 (11.2 g, 81.5 mmol) and dimethylamine (8.5 mL, 40%, 77.2 mmol) in H2O (60 mL) at 0° C. The mixture was stirred at 0-5° C. for 1 h and poured into ice cold water. The solution was extracted with chloroform (3×100 mL). The combined CHCl3 layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using hexane-EtOAc (90:10) as eluents to give the product as a pale brown color solid (3.8 g, 76%), mp 92-94° C. 1H NMR (400 MHz, DMSO-d6): δ 7.78-7.80 (2H, m), 7.64 (1H, s), 7.46-7.52 (3H, m), 3.84 (3H, s), 3.60 (3H, s), 3.28 (3H, s); LC-MS (positive ion mode): m/z 290 (M+H)+.

1. dissolutionto dissolve the product
2. stirringThe mixture was stirred at 0-5° C. for 1 h
3. additionpoured into ice cold water
4. extractionThe solution was extracted with chloroform (3×100 mL)
5. washThe combined CHCl3 layer was washed with water, brine
6. dry with materialdried over sodium sulfate
7. filtrationThe solution was filtered
8. customevaporated the solvent
9. customThe residue was chromatographed over silica gel column

ORD record

ord-5566c76925c74560906db40b0b51fc5c

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08258119B2