Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Sodium methanethiolate | HCID 4378561 | — |
| Reactant | HCID 54162932 | HCID 54162932 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 11419637 | HCID 11419637 | 62.5% |
Reaction Steps
Sodium methanethiolate (49.5 mg) was added to a solution of (R)-N-[2-chloro-4-(2-fluorophenylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Method 63) (0.15 g) in NMP (1.5 ml) and the mixture was heated at 120° C. for 18 hours then cooled. Saturated aqueous ammonium chloride solution (15 ml) was added and the mixture was extracted with ethyl acetate (2×50 ml). The organic extracts were combined, washed with brine and dried. Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column eluting with 0-20% ethyl acetate/hexane to give the title compound (0.10 g) as a solid. NMR: (CDCl3): 1.75 (s, 3H), 2.4 (s, 3H), 3.6 (brs, 1H), 7.3 (t, 1H), 7.35 (t, 1H), 7.55 (m, 1H), 7.9 (dd, 1H), 8.05 (d, 1H), 8.25 (dd, 1H), 8.6 (d, 1H), 9.25 (brs, 1H); MS (ESP−): 452.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06498275B1 |
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| Source dataset | uspto-grants-2002_12 |
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| ORD ID | ord-f861349da4e9432b99270bc50d139764 |
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| Source note | uspto-grants-2002_12 |
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