반응 #5331

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Methyl 3,4-diamino-5-methylthiophene-2-carboxylate

triphosgene

→

title compound

Methyl 1,3-dihydro-4-methyl-2-oxo-thieno[3,4-d]imidazole-6-carboxylate

용매

N,N-dimethyl formamide

dichloromethane

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후처리

1. 1
   기타precipitates
2. 2
   여과were collected by filtration
3. 3
   세척washed with dichloromethane
4. 4
   기타dried
5. 5
   workup.ADDITIONTo the suspension was added sodium hydride (60% in oil; 0.55 g)
6. 6
   workup.STIRRINGthe mixture was stirred for three days at room temperature
7. 7
   기타The solvent was evaporated under reduced pressure
8. 8
   workup.ADDITIONTo the residue was added 2N-HCl
9. 9
   기타Resulting
10. 10
    기타precipitates
11. 11
    여과were collected by filtration
12. 12
    세척washed with water, ether and methanol successively
13. 13
    기타by drying

실험 절차

Methyl 3,4-diamino-5-methylthiophene-2-carboxylate (3.0 g) was dissolved in a mixture of N,N-dimethyl formamide (5 ml) and dichloromethane (15 ml). To the solution was added triphosgene (2.4 g) in portions. The mixture was stirred for two days at room temperature, and precipitates were collected by filtration, washed with dichloromethane and dried. Resultant white powder (2.4 g) was suspended in N,N-dimethylformamide (25 ml). To the suspension was added sodium hydride (60% in oil; 0.55 g), and the mixture was stirred for three days at room temperature. The solvent was evaporated under reduced pressure. To the residue was added 2N-HCl. Resulting precipitates were collected by filtration, washed with water, ether and methanol successively, followed by drying to afford the title compound (82 g, 53%) as pale brown powder.

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