Diphosgene → 5-Methyl-2h-thieno[2,3-d][1,3]oxazine-2,4(1h)-dione

HRID 902521

반응식

HRID 902521 반응식
[OH-].[K+].[NH2:3][C:4]1[S:5][CH:6]=[C:7]([CH3:14])[C:8]=1[C:9]([O:11][CH2:12]C)=[O:10].ClC(OC(Cl)(Cl)Cl)=[O:17]>O>[CH3:14][C:7]1[C:8]2[C:9](=[O:10])[O:11][C:12](=[O:17])[NH:3][C:4]=2[S:5][CH:6]=1

참가 물질

5

반응물 3

HCID 10426DiphosgeneHCID 14797Potassium HydroxideHCID 521132Ethyl 2-amino-4-methylthiophene-3-carboxylate

생성물 1

HCID 587883805-Methyl-2h-thieno[2,3-d][1,3]oxazine-2,4(1h)-dione수율 67.2%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

Potassium hydroxide (14.77 g, 0.26 mol) was dissolved in 500 mL water. To this solution was added ethyl 2-amino-4-methyl-thiophene-3-carboxylate (24.38 g, 0.13 mol). The solution was heated at 100° C. for 16 hours. The solution was then cooled to 0° C. and trichloromethyl chloroformate (23.8 mL, 0.20 mol) was added slowly. The solution was allowed to come to room temperature and further stirred for 5 hours. The precipitated solid was collected by vacuum filtration to yield 16.0 g (66%) of 5-methyl-1H-thieno[2,3-d][1,3]oxazine-2,4-dione. MP 220° C. 1H-NMR (DMSO-d6) δ 2.30 (d, J=1.2 Hz, 3H), 6.78 (d, J=1.2 Hz, 1H), 12.55 (b, 1H) ppm; EIMS m/z 184 (M+1).

후처리

  1. temperatureThe solution was then cooled to 0° C.
  2. customto come to room temperature
  3. filtrationThe precipitated solid was collected by vacuum filtration

출처 및 근거

ORD 기록
ord-a5dfc9cde426436ea044192590aab6ba
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365200B2

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