Sodium Hydroxide → 2-(2-Furoylthio)acetamide
Reaction equation
C([NH:4][C:5](=[O:11])[CH2:6][S:7][C:8](=[O:10])[CH3:9])(=O)C.[OH-].[Na+].[O:14]1C=[CH:17][CH:16]=[C:15]1C(Cl)=O>CO>[O:14]1[CH:15]=[CH:16][CH:17]=[C:9]1[C:8]([S:7][CH2:6][C:5]([NH2:4])=[O:11])=[O:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A slurry was prepared from 8.75 g. (0.05 mole) of N-acetyl-2-(acetylthio)acetamide and 100 ml. of methanol at -5° C., and nitrogen was bubbled through the slurry. There was then added 2.0 g. (0.05 mole) of sodium hydroxide in 20 ml. of methanol. The reaction mixture was aged for 1 hour and then concentrated under high vacuum while the temperature was kept below 30° C. Next, 100 ml. of dimethylformamide was added and the reaction mixture was cooled to 0° C. There was then added 7.2 g. (0.055 mole) of 2-furoyl chloride, and the reaction mixture was aged for 3 hours at 0° C., after which it was concentrated under high vacuum. The residue was charged to a silica gel column and eluted with 50% ethylacetate/hexane. The product was recrystallized from toluene and air dried to yield 2.9 g., m.p. 126°-128° C.
Workup
- customA slurry was prepared from 8.75 g
- customof methanol at -5° C., and nitrogen was bubbled through the slurry
- additionThere was then added 2.0 g
- concentrationconcentrated under high vacuum while the temperature
- customwas kept below 30° C
- additionof dimethylformamide was added
- additionThere was then added 7.2 g
- concentrationafter which it was concentrated under high vacuum
- additionThe residue was charged to a silica gel column
- washeluted with 50% ethylacetate/hexane
- customThe product was recrystallized from toluene and air
- customdried
- customto yield 2.9 g
Sources & evidence
- ORD record
- ord-ed99dd1653194b009c1574a4b55eb24b
- Source dataset
- uspto-grants-1982_05
- Patent number
- US04329363
Reaction notes
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