Pyridine → HCID 2807639, compound
Reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].N1C=CC=CC=1.[C:17]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl>[C:17]([C:21]1[CH:22]=[CH:23][C:24]([C:25]([NH:1][C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7]([O:9][CH3:10])=[O:8])=[O:26])=[CH:28][CH:29]=1)([CH3:20])([CH3:18])[CH3:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A flame dried flask was charged with methyl 3-amino-2-thiophenecarboxylate (5.0 g, 35.0 mmol), pyridine (2.82 mL, 35.0 mmol), and dry methylene chloride (160 mL). The solution was cooled to 0 ° C. and 4-tert-butylbenzoyl chloride (6.21 mL, 31.8 mmol) was added. After 1 h, the solvent was removed in vacuo and the remaining material was dissolved in ethyl acetate. The organic phase was washed four times with water and once with brine. The organic phase was then dried over magnesium sulfate, filtered, and the solvent removed in vacuo. The crude product was purified by column chromatography over silica gel using an eluent of 2% ethyl acetate in hexane and 5% ethyl acetate in hexane to afford the product (9.67g, 96% yield).
Workup
- customA flame dried flask
- customthe solvent was removed in vacuo
- dissolutionthe remaining material was dissolved in ethyl acetate
- washThe organic phase was washed four times with water
- dry with materialThe organic phase was then dried over magnesium sulfate
- filtrationfiltered
- customthe solvent removed in vacuo
- customThe crude product was purified by column chromatography over silica gel using an eluent of 2% ethyl acetate in hexane and 5% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-88bc835ef87c430685af9d01bd42a1aa
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06500851B2
Reaction notes
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