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

HRID 9103

反応式

HRID 9103 の反応式
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH2:13]([N:15]=[C:16]=[O:17])[CH3:14].C(N(CC)CC)C>CN(C)C=O>[C:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:1][C:16]([NH:15][CH2:13][CH3:14])=[O:17])[S:3][C:4]=2[CH:10]=1)#[N:12]

参加物

5

反応物 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 43271392-Aminobenzothiazole-6-carbonitrile

生成物 1

HCID 21985533N-(6-Cyano-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

2-Amino-1,3-benzothiazole-6-carbonitrile (0.2 g) was dissolved in about 5 mL dimethylformamide. About 0.2 mL of ethylisocyanate was added, followed by about 0.3 mL triethylamine and the solution was heated to about 80° C. under good agitation. The solution was allowed to stir for about 4 hours then cooled to room temperature. The solvent was removed in vacuo and the solids were washed well with ether. The product was further purified by column chromatography and after drying in vacuo, about 0.14 grams was isolated. 1H NMR 1.1 (t, 3H, J=7.2 Hz), 3.2 (m, 2H), 6.8 (s, 1H), 7.7 (m, 2H), 8.4 (s, 1H), 11.0 (s, 1H), LC/MS 2.54 min, 247 (MH+), 245 (M−H−), lab RP-HPLC RT 7.8 minutes.

後処理

  1. temperaturethen cooled to room temperature
  2. customThe solvent was removed in vacuo
  3. washthe solids were washed well with ether
  4. customThe product was further purified by column chromatography
  5. customafter drying in vacuo
  6. customabout 0.14 grams was isolated
  7. custom1H NMR 1.1 (t, 3H, J=7.2 Hz), 3.2 (m, 2H), 6.8 (s, 1H), 7.7 (m, 2H), 8.4 (s, 1H), 11.0 (s, 1H), LC/MS 2.54 min, 247 (MH+), 245 (M−H−), lab RP-HPLC RT 7.8 minutes

出典と根拠

ORDレコード
ord-4bb201544c5043cd978fe2b16f5062ab
出典データセット
uspto-grants-2006_08
特許番号
US07091227B2

関連ノート

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