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

HRID 1099100ノート

反応式

HRID 1099100 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
15 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b49d38916fc2436091bf798f91c3fa5e
出典データセット
uspto-grants-2012_03
特許番号
US08143395B2

反応ノート

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