Nitric Acid → N-(6-Chloro-5-nitro-1,3-benzothiazol-2-yl)-N'-ethylurea

HRID 9099

反応式

HRID 9099 の反応式
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[CH:3]=1.[N+:17]([O-])([OH:19])=[O:18]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[CH:3]=1

参加物

4

反応物 2

HCID 944Nitric AcidHCID 9964976N-(6-Chloro-1,3-benzothiazol-2-yl)-N'-ethylurea

生成物 1

HCID 9922382N-(6-Chloro-5-nitro-1,3-benzothiazol-2-yl)-N'-ethylurea

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

実験手順

Three grams of N-(6-chloro-1,3-benzothiazol-2-yl)-N′-ethylurea was dissolved in about 15 mL of concentrated sulfuric acid (about 92–94%). The solution was cooled to about 0–5° C. About 1.5 g of ice cooled nitric acid (70% concentration was used, though this is not necessary) was added dropwise. The reaction was held at 0–5° C. for about one hour then poured into water. The pH was then adjusted to about 7–8 with ammonia and the solids were isolated by filtration. The solids were washed with water then dried in vacuo. The product was further purified by chromatography then dried in vacuo. 1H NMR 1.08 (t, 3H, J=7.2 Hz), 3.19 (m, 2H), 6.92 (br s, 1H), 8.26 (s, 1H), 8.31 (s, 1H), LC/MS 3.72 min, 302 (M+1)

後処理

  1. temperatureThe solution was cooled to about 0–5° C
  2. concentration70% concentration
  3. additionwas added dropwise
  4. additionthen poured into water
  5. customthe solids were isolated by filtration
  6. washThe solids were washed with water
  7. customthen dried in vacuo
  8. customThe product was further purified by chromatography
  9. customthen dried in vacuo
  10. custom1H NMR 1.08 (t, 3H, J=7.2 Hz), 3.19 (m, 2H), 6.92 (br s, 1H), 8.26 (s, 1H), 8.31 (s, 1H), LC/MS 3.72 min, 302 (M+1)

出典と根拠

ORDレコード
ord-8fdf60b6ede54c5a9ab0db4f301291f1
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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