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

HRID 1707709

반응식

HRID 1707709 반응식
[NH2:1][C:2]1[C:6]([NH2:7])=[C:5]([CH3:8])[S:4][C:3]=1[C:9]([O:11][CH3:12])=[O:10].Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl>CN(C)C=O.ClCCl>[CH3:8][C:5]1[S:4][C:3]([C:9]([O:11][CH3:12])=[O:10])=[C:2]2[C:6]=1[NH:7][C:14](=[O:16])[NH:1]2

참가 물질

5

반응물 2

HCID 94429TriphosgeneHCID 18693138Methyl 3,4-diamino-5-methylthiophene-2-carboxylate

생성물 1

HCID 18693187Methyl 1,3-dihydro-4-methyl-2-oxo-thieno[3,4-d]imidazole-6-carboxylate수율 4,777.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

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-HC1. 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.

후처리

  1. customprecipitates
  2. filtrationwere collected by filtration
  3. washwashed with dichloromethane
  4. customdried
  5. additionTo the suspension was added sodium hydride (60% in oil; 0.55 g)
  6. stirringthe mixture was stirred for three days at room temperature
  7. customThe solvent was evaporated under reduced pressure
  8. additionTo the residue was added 2N-HC1
  9. customResulting
  10. customprecipitates
  11. filtrationwere collected by filtration
  12. washwashed with water, ether and methanol successively
  13. customby drying

출처 및 근거

ORD 기록
ord-aa87b96de60e47e78b81236a55941eda
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05354766

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