Ethyl isocyanate → N-(6-Methylcyano-1,3-benzothiazol-2-yl)-N'-ethylurea

HRID 9177ノート

反応式

HRID 9177 の反応式
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH2:11]C#N)[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH2:14]([N:16]=[C:17]=[O:18])[CH3:15].[CH2:19]([N:21](CC)CC)C>CN(C)C=O>[CH3:11][C:9]1[CH:8]=[C:7]([C:19]#[N:21])[C:5]2[N:6]=[C:2]([NH:1][C:17]([NH:16][CH2:14][CH3:15])=[O:18])[S:3][C:4]=2[CH:10]=1

参加物

5

反応物 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 21298164(2-Amino-1,3-benzothiazol-6-yl)acetonitrile

生成物 1

HCID 21985550N-(6-Methylcyano-1,3-benzothiazol-2-yl)-N'-ethylurea

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

About 1 g of (2-amino-1,3-benzothiazol-6-yl)methyl cyanide is dissolved in about 10 ml dimethylformamide. About 0.8 ml of ethylisocyanate is added followed by about 1.4 ml triethylamine and the solution is heated to about 80° C. under good agitation. The solution is allowed to stir for about 4–6 hours then cooled to RT. The solvent is removed in vacuo and the solids are washed well with ether. The product is recrystallized from hot EtOAc. 1H NMR 1.09 (t, 3H), 3.1 (m, 2H), 4.1 (s, 2H), 6.72 (m, 1H), 7.32 (m, 1H), 7.61 (d, 1H), 7.85 (s, 1H), 10.7 (s, 1H); LC/MS 2.73 min, 261 (M+1), 259 (M−1).

後処理

  1. temperaturethen cooled to RT
  2. customThe solvent is removed in vacuo
  3. washthe solids are washed well with ether
  4. customThe product is recrystallized from hot EtOAc
  5. customLC/MS 2.73 min, 261 (M+1), 259 (M−1)

出典と根拠

ORDレコード
ord-157697f4a0e64340ac2d0e8d298b748a
出典データセット
uspto-grants-2006_08
特許番号
US07091227B2

反応ノート

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