4'-Mercaptoacetanilide → HCID 178474281, compound

HRID 1987607Notes

Reaction equation

HRID 1987607 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]([CH:18]([CH3:20])[CH3:19])=[N:14][NH:15][C:16]/2=[O:17])/[CH:3]=1.[C:21]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([SH:31])=[CH:27][CH:26]=1)(=[O:23])[CH3:22]>C(O)C>[CH: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:31][C:28]3[CH:27]=[CH:26][C:25]([NH:24][C:21](=[O:23])[CH3:22])=[CH:30][CH:29]=3)=[CH:3]\1)=[CH:10][CH:9]=[CH:8][CH:7]=2)([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 707774'-MercaptoacetanilideHCID 178440351HCID 178440351, compound

Product 1

HCID 178474281HCID 178474281, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
180 °C

Procedure

(Z)-4-(4-chloroquinolin-2(1H)-ylidene)-3-isopropyl-1H-pyrazol-5(4H)-one (0.029 g, 0.089 mmol) was dissolved in ethanol (1 mL) and 4-acetamidothiophenol (0.016 g, 0.094 mmol) was added. The reaction mixture was heated to 180° C. using a microwave reactor for 30 minutes. The mixture was then concentrated and purified by LC-MS to give Example 19. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.96 (d, J=6.82 Hz, 6H) 2.13 (s, 3H) 2.53 (bs, 1H) 6.65 (s, 1H) 7.68-7.70 (m, 3H) 7.86-7.97 (m, 3H) 8.02 (s, 1H) 8.20 (d, J=8.34 Hz, 1H) 10.43 (s, 1H); ESI-MS: m/z calc'd for C23H22N4O2S 418.51. found 419.3 (M+H)+.

Workup

  1. customfor 30 minutes
  2. concentrationThe mixture was then concentrated
  3. custompurified by LC-MS
  4. customto give Example 19

Sources & evidence

ORD record
ord-139d008af635428a945607c4fba040ee
Source dataset
uspto-grants-2009_06
Patent number
US07550598B2

Reaction notes

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