Ethyl isothiocyanatoformate → Ethyl [(2-chloro-5-methoxypyrimidin-4-yl)amino]carbonothioylcarbamate

HRID 1099100노트

반응식

HRID 1099100 반응식
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][CH3:10])=[CH:4][N:3]=1.[CH3:11][CH2:12][O:13][C:14]([N:16]=[C:17]=[S:18])=[O:15]>C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:17]([NH:16][C:14](=[O:15])[O:13][CH2:12][CH3:11])=[S:18])[C:5]([O:9][CH3:10])=[CH:4][N:3]=1

참가 물질

4

반응물 2

HCID 85320Ethyl isothiocyanatoformateHCID 569495382-Chloro-5-methoxypyrimidin-4-amine

생성물 1

HCID 56949522Ethyl [(2-chloro-5-methoxypyrimidin-4-yl)amino]carbonothioylcarbamate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
15 °C

실험 절차

2-Chloro-5-methoxypyrimidin-4-amine (1) (6.4 g, 0.040 mol) was suspended in ethyl acetate (100 mL) and heated to near reflux. Ethyl isothiocyanatidocarbonate (8.9 g, 1.7 eq) was added all at once, and the mixture was maintained at reflux for 10 hours. The resulting slurry was cooled to 15° C., and the solid product was isolated by filtration and the cake washed with fresh ethyl acetate to afford the title compound in several crops as a solid (7.8 g, 67%): mp 182° C.; 1H NMR (DMSO-d6): δ 11.97 (s, 1H), 11.72 (s, 1H), 8.50 (s, 1H), 4.22 (q, 2H), 3.72 (s, 3H), 1.17 (t, 3H); 13C NMR (DMSO-d6): δ 177.82, 153.58, 150.00, 149.01, 144.26, 142.63, 62.76, 57.56, 14.44; Mass spec (accurate mass): Calcd for C9H11ClN4O3S: 290.024039; found, 290.0241.

후처리

  1. temperatureheated
  2. temperatureto near reflux
  3. temperaturewas maintained
  4. temperatureat reflux for 10 hours
  5. customthe solid product was isolated by filtration
  6. washthe cake washed with fresh ethyl acetate

출처 및 근거

ORD 기록
ord-b49d38916fc2436091bf798f91c3fa5e
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143395B2

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