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

HRID 2415626Notes

Reaction equation

HRID 2415626 reaction equation
[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

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 178477879HCID 178477879, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6b97aaae65f549c4a473c0d6f53209fc
Source dataset
uspto-grants-2004_11
Patent number
US06818772B2

Reaction notes

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