Benzoyl chloride → 2,6-Diethyl-4-nitrophenylthiourea

HRID 329603

反応式

HRID 329603 の反応式
[S-:1][C:2]#[N:3].[K+].C(Cl)(=O)C1C=CC=CC=1.[CH2:14]([C:16]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[C:19]([CH2:26][CH3:27])[C:17]=1[NH2:18])[CH3:15].[OH-].[Na+]>CC(C)=O.O.C(O)C>[CH2:26]([C:19]1[CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=[C:16]([CH2:14][CH3:15])[C:17]=1[NH:18][C:2]([NH2:3])=[S:1])[CH3:27]

参加物

8

反応物 4

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 516872Potassium thiocyanateHCID 81426772,6-Diethyl-4-nitroaniline

生成物 1

HCID 538496572,6-Diethyl-4-nitrophenylthiourea収率 59.2%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To 2.34 g (24.1 mmol) of potassium thiocyanate in 30 ml of acetone was added 2.32 ml (20.0 mmol) of benzoyl chloride. The mixture was then refluxed for 15 min, cooled to r.t., and 3.16 g (16.3 mmol) of 2,6-diethyl-4-nitroaniline obtained from step C was added. The mixture was then refluxed for 15 min, cooled to r.t., and poured into 200 ml of ice-water. The precipitate was collected and washed with water, then dissolved in a solution comprising 0.70 g (18 mmol) of sodium hydroxide in 5 ml of water and 50 ml of ethanol. The solution was refluxed for 1 hr, cooled to r.t., poured into icewater, then the precipitate was collected, washed with water several times, and dried. The solids were then triturated with ethyl acetate to yield 2.44 g (59.2%) of product. NMR (CDCl3, d6 -DMSO):δ 1.30 (t, 6H), 2.74 (q, 4H), 6.9 (b, 2H), 7.98 (s, 2H), 9 (b, 1H).

後処理

  1. temperatureThe mixture was then refluxed for 15 min
  2. temperatureThe mixture was then refluxed for 15 min
  3. temperaturecooled to r.t.
  4. customThe precipitate was collected
  5. washwashed with water
  6. temperatureThe solution was refluxed for 1 hr
  7. temperaturecooled to r.t.
  8. additionpoured into icewater
  9. customthe precipitate was collected
  10. washwashed with water several times
  11. customdried
  12. customThe solids were then triturated with ethyl acetate

出典と根拠

ORDレコード
ord-e0d9d0f0845d47f9bdc2f5af4d61b2b2
出典データセット
uspto-grants-1990_01
特許番号
US04892871

関連ノート

読み込み中…