Thiophenol → HCID 178434121, compound

HRID 1987597Notes

Reaction equation

HRID 1987597 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5]/[C:4](=[C:12]2/[C:13]([CH3:18])=[N:14][NH:15][C:16]/2=[O:17])/[CH:3]=1.[C:19]1([SH:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[CH3:18][C:13]1=[N:14][NH:15][C:16](=[O:17])/[C:12]/1=[C:4]1\[NH:5][C:6]2[C:11]([C:2]([S:25][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:3]\1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

4

Reactant 2

HCID 7969ThiophenolHCID 178434119HCID 178434119, compound

Product 1

HCID 178434121HCID 178434121, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
180 °C

Procedure

(Z)-4-(4-chloroquinolin-2(1H)-ylidene)-3-methyl-1H-pyrazol-5(4H)-one (0.05 g, 0.19 mmol) and thiophenol (Aldrich) (0.04 mL, 0.38 mmol) were dissolved in ethanol (2 mL). The reaction mixture was heated to 180° C. using a microwave reactor for 20 minutes. The solid was precipitated upon cooling. The material was filtered and washed with a minimal amount of ethanol, and then dried in vacuo. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.86 (s, 3H) 6.77 (s, 1H) 7.56 (t, J=7.58 Hz, 1H) 7.62 (s, 1H) 7.63 (d, J=2.53 Hz, 2H) 7.71-7.76 (m, 2H) 7.79 (t, J=7.58 Hz, 1H) 7.84-7.89 (m, 1H) 8.08 (d, J=8.34 Hz, 1H); ESI-MS: m/z calc'd for C19H15N3OS 333.09. found 334.2 (M+H)+.

Workup

  1. customfor 20 minutes
  2. customThe solid was precipitated
  3. temperatureupon cooling
  4. filtrationThe material was filtered
  5. washwashed with a minimal amount of ethanol
  6. customdried in vacuo

Sources & evidence

ORD record
ord-99dfe9c74e37459e8964142b4ce01bcc
Source dataset
uspto-grants-2009_06
Patent number
US07550598B2

Reaction notes

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