Trifluoroacetic acid → HCID 178510544, compound
Reaction equation
[C:1]1([O:7][C:8](=[O:27])[NH:9][C:10]2[S:14][N:13]=[C:12]([S:15]CC3C=CC(OC)=CC=3)[C:11]=2[C:25]#[N:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>>[C:1]1([O:7][C:8](=[O:27])[NH:9][C:10]2[S:14][N:13]=[C:12]([SH:15])[C:11]=2[C:25]#[N:26])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Procedure
To a mixture of [4-cyano-3-(4-methoxy-benzylsulfanyl)-isothiazol-5-yl)-carbamic acid phenyl ester (1.0 g, 2.5 mmol), trifluoracetic acid (26 mL) and anisole (2.7 g, 25 mmol) at 0° C. was added mercuric acetate (0.80 g, 2.5 mmol). The mixture was allowed to warm to room temperature overnight. After concentration in vacuo, the mixture was diluted with 100 mL of water and 100 mL of ethyl acetate. Hydrogen sulfide was bubbled in slowly until precipitation of the mercury salts was complete. The mixture was diluted with brine, extracted 3× with 200 mL of ethyl acetate, and the combined organic layers were filtered through celite, dried over Na2SO4, filtered and concentrated in vacuo, affording 0.70 g (100%) of (4-cyano-3-mercapto-isothiazol-5-yl)-carbamic acid phenyl ester as a colorless solid. 1H NMR (400 MHz, acetone-d6) δ 7.47 (t, 2H, J=7.6 Hz), 7.35-7.30 (m, 3H) ppm; MS (APCI, m/z): 276 [M−H]−.
Workup
- concentrationAfter concentration in vacuo
- additionthe mixture was diluted with 100 mL of water and 100 mL of ethyl acetate
- customHydrogen sulfide was bubbled in
- customslowly until precipitation of the mercury salts
- additionThe mixture was diluted with brine
- extractionextracted 3× with 200 mL of ethyl acetate
- filtrationthe combined organic layers were filtered through celite
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b2d269e042054d4686e7b49e73cb57fe
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07790902B2
Reaction notes
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