Ethanol → HCID 29945563, compound
Reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[C:12]([O:24][CH3:25])[CH:11]=2)=[O:8])=[C:4]([N+:26]([O-])=O)[CH:3]=1.O.[Sn](Cl)(Cl)(Cl)Cl.[CH2:35](O)C>>[Br:1][C:2]1[S:6][C:5]2[C:7](=[O:8])[N:9]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[C:12]([O:24][CH3:25])[CH:11]=3)[CH:35]=[N:26][C:4]=2[CH:3]=1Participants
Procedure
5-Bromo-N-[3-methoxy-4-(pyrrolidin-1ylethoxy)phenyl]-3-nitrothiophene-carboxamide (0.2926 g, 0.6239 mmol) was dissolved in ethanol (10 mL). Tin chloride monohydrate (0.7038 g, 3.1195 mmol) was added and the reaction was heated to reflux. Stirred for 30 min, cooled to RT and concentrated. Ethyl acetate (20 mL) and a saturated solution of Rochelle's salts (20 mL) were added and the mixture was stirred for 2 h. Organics were removed and dried over MgSO4, filtered and concentrated. The residue was taken up in formic acid (5 mL), stirred at reflux for 1 h, and then concentrated to give 0.1182 g (0.2633 mmol, 42%) of the product. 1H NMR (CDCl3) δ 8.03 (s, 1H), 7.38 (s, 1H), 7.01 d, 1H J=8.4 Hz), 6.92-6.88 (m, 2H)), 4.41 (t, 2H, J=5.0 Hz), 3.85 (s, 3H), 3.44 (t, 2H, J=5.0 Hz), 3.28-3.2 (bs, 4H), 2.01-1.9 (bs, 4H).
Workup
- temperaturethe reaction was heated to reflux
- concentrationconcentrated
- additionEthyl acetate (20 mL) and a saturated solution of Rochelle's salts (20 mL) were added
- stirringthe mixture was stirred for 2 h
- customOrganics were removed
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- stirringstirred
- temperatureat reflux for 1 h
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0a97abfbbf154475abcc9d504e810530
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07285557B2
Reaction notes
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