2-Amino-4-chlorophenol → HCID 178527795, compound

Temperature

0 °C

2-Amino-4-chlorophenol (2.50 kg, 17.4 mol) was charged to a vessel and suspended in water (52 L) and methanol (10.4 L). High dilution was required to prevent slow and difficult filtration of the product. The mixture was stirred, cooled to 0° C., then thiophosgene (2.00 kg, 17.4 mol) was added to the suspension ensuring that the internal temperature remained at 5° C. throughout the addition. Water (8 L) and methanol (2 L) were added to aid stirring and the slurry was warmed to 13° C. for 1 h, followed by aging at 20° C. for a further 1 h. The slurry was then filtered and the solid washed with water (5 L). The batch was repeated and combined to dry in a vacuum oven (T=40° C.) for 15 h to give 9a (5.81 kg, 31.3 mol). The data corresponds to the commercially available material. 1H NMR (400 MHz, d6-DMSO): δ 7.51 (d, 1 H, J=9.2 Hz), 7.3 07.26 (m, 2 H), 13C NMR (100.6 MHz, d6-DMSO): δ 181.2, 147.4, 133.1, 129.7, 123.9, 111.6, 110.8. HRMS (ESI): m/z [M++H] calcd for C7H4ClNOS: 185.9780. found: 185.9785.

1. filtrationdifficult filtration of the product
2. additionremained at 5° C. throughout the addition
3. stirringstirring
4. temperaturethe slurry was warmed to 13° C. for 1 h
5. filtrationThe slurry was then filtered
6. washthe solid washed with water (5 L)
7. customto dry in a vacuum oven (T=40° C.) for 15 h

ORD record

ord-f0db1507745c49fba45b700299352126

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108959B2