4'-Mercaptoacetanilide → HCID 178440362, compound

HRID 1987612Notes

Reaction equation

HRID 1987612 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]([CH2:18][CH2:19][CH3:20])=[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>[O:17]=[C:16]1[NH:15][N:14]=[C:13]([CH2:18][CH2:19][CH3:20])/[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

Participants

4

Reactant 2

HCID 707774'-MercaptoacetanilideHCID 178440352HCID 178440352, compound

Product 1

HCID 178440362HCID 178440362, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
180 °C

Procedure

(Z)-4-(4-chloroquinolin-2(1H)-ylidene)-3-propyl-1H-pyrazol-5(4H)-one (0.045 g, 0.013 mmol) was dissolved in ethanol (1.5 mL) and 4-acetamidothiophenol (0.023 g, 0.013 mmol) was added. The reaction mixture was heated to 180° C. using a microwave reactor for 5-10 minutes. The mixture was then concentrated and the resulting solid filtered and washed with ether. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.70 (t, J=7.33 Hz, 3H) 1.32 (qd, J=7.45, 7.20 Hz, 2H) 2.11 (s, 3H) 2.25 (t, J=7.07 Hz, 2H) 6.76 (s, 1H) 7.63-7.71 (m, 3H) 7.89 (t, J=8.84 Hz, 3H) 7.93-7.99 (m, 1H) 8.17 (d, J=8.34 Hz, 1H) 10.36 (s, 1H); ESI-MS: m/z calc'd for C23H22N4O2S 418.51. found 419.3 (M+H)+.

Workup

  1. customfor 5-10 minutes
  2. concentrationThe mixture was then concentrated
  3. filtrationthe resulting solid filtered
  4. washwashed with ether

Sources & evidence

ORD record
ord-4cfaadaa026749d0922d20af6734ee7a
Source dataset
uspto-grants-2009_06
Patent number
US07550598B2

Reaction notes

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