Aniline → HCID 18537266, compound
Reaction equation
[CH3:1][S:2][C:3]1[S:7]C(C(OC)=O)=[CH:5][C:4]=1[C:12](=[O:20])NC1C=CC=CC=1.COC(C1SC(C)=C(C(O)=S)C=1)=O.C(Cl)(=O)C([Cl:37])=O.C([N:43]([CH2:47][CH3:48])C(C)C)(C)C.[NH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.C[N:57](C=O)C>C(Cl)Cl.CCOC(C)=O>[ClH:37].[CH3:1][S:2][C:3]1[S:7][C:48]([C:47]([NH2:43])=[NH:57])=[CH:5][C:4]=1[C:12](=[O:20])[NH:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Procedure
Methyl 5-methylthio-4-(N-phenylcarbamoyl)thiophene-2-carboxylate: To 182 mg (0.785 mmol) of 5-(methoxycarbonyl)-2-methylthiothiophene-3-carboxylic acid (as prepared in Example 95) in 4 mL of anhyd CH2Cl2 was treated with 275 μL (3.15 mmol) of oxalyl chloride and 6 μL of anhyd DMF for 2 h similar to Example 79, step (a); followed by 206 μL (1.18 mmol) of N,N-diisopropylethylamine and 85.9 μL (0.942 mmol) of aniline in 3 mL of anhyd CH2Cl2 for 20 min. The mixture was poured into 25 mL of EtOAc and washed with 1 M HCl (2×25 mL), saturated NaHCO3 (2×25 mL), and brine (25 mL), and dried over Na2SO4. Removal of the solvent in vacuo, afforded the pure title compound as a light yellow solid (163 mg, 68%). 1H-NMR (300 MHz, CDCl3) δ 8.23 (broad s, 1H), 8.10 (s, 1H), 7.63 (d, 2H, J=7 Hz), 7.36 (t, 2H, J=7 Hz), 7.15 (t, 2H, J=7 Hz), 3.90 (s, 3H), and 2.64 (s, 3H).
Workup
- washwashed with 1 M HCl (2×25 mL), saturated NaHCO3 (2×25 mL), and brine (25 mL)
- dry with materialdried over Na2SO4
- customRemoval of the solvent in vacuo
Sources & evidence
- ORD record
- ord-e700a50aa00d4717a622d080df53a8a4
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06515002B2
Reaction notes
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