Water → N-{4-((7-chloroquinolin-4-yl)amino)cyclohexyl}thiourea

HRID 2415626ノート

反応式

HRID 2415626 の反応式
[S-:1][C:2]#[N:3].[NH4+:4].C(Cl)(=O)C1C=CC=CC=1.[Cl:14][C:15]1[CH:24]=[C:23]2[C:18]([C:19]([NH:25][C@H:26]3[CH2:31][CH2:30][C@@H:29](NC4C5C(=CC(Cl)=CC=5)N=CC=4)[CH2:28][CH2:27]3)=[CH:20][CH:21]=[N:22]2)=[CH:17][CH:16]=1.O>CC(C)=O>[Cl:14][C:15]1[CH:24]=[C:23]2[C:18]([C:19]([NH:25][CH:26]3[CH2:31][CH2:30][CH:29]([NH:3][C:2]([NH2:4])=[S:1])[CH2:28][CH2:27]3)=[CH:20][CH:21]=[N:22]2)=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 178477879HCID 178477879、化合物

生成物 1

HCID 22641824N-{4-((7-chloroquinolin-4-yl)amino)cyclohexyl}thiourea収率 47%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒3 回

実験手順

Ammonium thiocyanate (320 mg, 4.2 mmol) was dissolved in 85 mL dry acetone. A solution of benzoyl chloride (590 mg, 4.2 mmol) in 10 mL dry acetone was added dropwise and heated at reflux for 30 minutes. A solution of 23A cis-N,N′-bis(7-chloroquinolin-4-yl)cyclohexane-1,4-diamine (1 g, 3.6 mmol) in 10 mL dry acetone was added dropwise to the refluxing solution. After the addition, the solution was poured into 100 mL of water. The resulting solid was filtered and heated in 30 mL of 10% sodium hydroxide until dissolved. The solution was then allowed to cool and was placed in the freezer overnight. The white solid was filtered and dried under vacumn to give 565 mg, 47% yield. MS ESI(+)Q1MS m/z 334 (M+H)+; 1 H NMR (300 MHz, DMSO) δ ppm 8.38-8.42 (m, 2 H), 8.78 (d, 1 H), 7.44 (dd, 1 H), 6.66-6.69 (m, 2 H), 6.53 (d, 1 H), 4.17 (m, 1 H), 3.61 (m, 1 H), 1.96-2.06 (m, 4H), 1.65-1.84 (m, 8 H).

後処理

  1. temperatureheated
  2. temperatureat reflux for 30 minutes
  3. additionAfter the addition
  4. filtrationThe resulting solid was filtered
  5. temperatureheated in 30 mL of 10% sodium hydroxide
  6. dissolutionuntil dissolved
  7. temperatureto cool
  8. customwas placed in the freezer overnight
  9. filtrationThe white solid was filtered
  10. customdried under vacumn
  11. customto give 565 mg, 47% yield

出典と根拠

ORDレコード
ord-6b97aaae65f549c4a473c0d6f53209fc
出典データセット
uspto-grants-2004_11
特許番号
US06818772B2

反応ノート

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