Hydrochloric Acid → HCID 22287472, compound

A solution of 2-amino-4-(4-acetamidophenylsulphanyl)nitrobenzene (Method 15) (2.4 g) in warm glacial acetic acid (15 ml) was poured onto ice (24 ml). Concentrated hydrochloric acid (4.5 ml) was added and the mixture was stirred and cooled to <5° C. A solution of sodium nitrite (0.601 g) in water (5 ml) was added over 7 minutes and the mixture was stirred for 2 hours at 0-5° C. Aqueous sulphamic acid solution (10% w/v) was added until a negative starch iodide test was observed. In a separate flask toluene was added to a solution of cuprous chloride (0.852 g) in water (1.2 ml) and concentrated hydrochloric acid (1.3 ml) and the mixture was cooled to <0° C. The first preparation (diazonium salt) was then added to the cold cuprous chloride mixture over 5 minutes and the resultant mixture was stirred at ambient temperature for 18 hours. The organic layer was separated and the aqueous layer was extracted with toluene (3×10 ml). The organic extracts were combined, washed with water and brine then dried. Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column eluting with 0-15% ethyl acetate/hexane to give the title compound (0.789 g). NMR: 2.1 (s, 3H), 7.1 (dd, 1H), 7.3 (d, 1H), 7.5 (d, 2H), 7.7 (d, 2H), 7.95 (d, 1H), 10.2 (brs, 1H).

1. temperaturecooled to <5° C
2. stirringthe mixture was stirred for 2 hours at 0-5° C
3. temperaturethe mixture was cooled to <0° C
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted with toluene (3×10 ml)
6. washwashed with water and brine
7. customthen dried
8. customVolatile material was removed by evaporation
9. customthe residue was purified by chromatography on a silica gel Mega Bond Elut column
10. washeluting with 0-15% ethyl acetate/hexane

ORD record

ord-e5b7f955480c45d9925571f22bd84f10

Source dataset

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06960688B2