4'-Mercaptoacetanilide → HCID 178440364, compound

HRID 1987632Notes

Reaction equation

HRID 1987632 reaction equation
C(C1CC(=O)NN=1)CC.ClC1C2C(=CC=C(OC)C=2)[N+]([O-])=CC=1.Cl[C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([O:35][CH3:36])[CH:33]=2)[NH:28]/[C:27](=[C:37]2/[C:38]([CH2:43][CH2:44][CH3:45])=[N:39][NH:40][C:41]/2=[O:42])/[CH:26]=1.[C:46]([NH:49][C:50]1[CH:55]=[CH:54][C:53]([SH:56])=[CH:52][CH:51]=1)(=[O:48])[CH3:47]>C(OC(=O)C)(=O)C.C(O)C>[CH3:36][O:35][C:32]1[CH:33]=[C:34]2[C:29](=[CH:30][CH:31]=1)[NH:28]/[C:27](=[C:37]1/[C:38]([CH2:43][CH2:44][CH3:45])=[N:39][NH:40][C:41]/1=[O:42])/[CH:26]=[C:25]2[S:56][C:53]1[CH:52]=[CH:51][C:50]([NH:49][C:46](=[O:48])[CH3:47])=[CH:55][CH:54]=1

Participants

7

Reactant 4

HCID 707774'-MercaptoacetanilideHCID 2692443-Propyl-1,4-dihydropyrazol-5-oneHCID 690548584-Chloro-6-methoxyquinoline 1-oxideHCID 178440355HCID 178440355, compound

Product 1

HCID 178440364HCID 178440364, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
180 °C

Procedure

3-Propyl-1H-pyrazol-5(4H)-one (1.16 mmol) and 4-chloro-6-methoxyquinoline 1-oxide (0.15 g, 1.16 mmol) were stirred in acetic anhydride (3 mL) at ambient temperature for 30-40 minutes. The reaction mixture was concentrated and the resulting solid was filtered off and washed with a minimum amount of ether. (Z)-4-(4-chloro-6-methoxyquinolin-2(1H)-ylidene)-3-propyl-1H-pyrazol-5(4H)-one (0.06 g, 0.016 mmol) was dissolved in ethanol (1.5 mL) and 4-acetamidothiophenol (0.028 g, 0.016 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 to give Example 45. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.71 (t, J=7.33 Hz, 3H) 1.27-1.37 (m, J=7.48, 7.48, 7.48, 7.48, 7.48 Hz, 2H) 2.11 (s, 3H) 2.31 (t, J=7.45 Hz, 2H) 3.96 (s, 3H) 6.83 (s, 1H) 7.42 (d, J=2.78 Hz, 1H) 7.57 (dd, J=9.09, 2.27 Hz, 1H) 7.68 (d, J=8.59 Hz, 2H) 7.87 (d, J=8.59 Hz, 2H) 8.00 (d, J=9.35 Hz, 1H) 10.36 (s, 1H); ESI-MS: m/z calc'd for C24H24N4O3S 448.54. found 449.2 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationthe resulting solid was filtered off
  3. washwashed with a minimum amount of ether
  4. customfor 5-10 minutes
  5. concentrationThe mixture was then concentrated
  6. filtrationthe resulting solid filtered
  7. washwashed with ether
  8. customto give Example 45

Sources & evidence

ORD record
ord-675fb440ad304c4aa6a59f5f9fd5f6b8
Source dataset
uspto-grants-2009_06
Patent number
US07550598B2

Reaction notes

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