Water → HCID 21933988, compound

HRID 891351Notes

Reaction equation

HRID 891351 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13](=[O:14])[C:12](OS(C3C=CC(C)=CC=3)(=O)=O)=[C:11]([C:26]3[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][CH:27]=3)[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[C:36]1(C)[C:41]([SH:42])=[CH:40][CH:39]=[CH:38][CH:37]=1.[C:44]([O-])([O-])=O.[K+].[K+].O>CCO>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13](=[O:14])[C:12]([S:42][C:41]3[CH:36]=[CH:37][C:38]([CH3:44])=[CH:39][CH:40]=3)=[C:11]([C:26]3[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][CH:27]=3)[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 87122-ThiocresolHCID 11430Potassium CarbonateHCID 219340222-(3-Chlorophenyl)-4-tosyloxy-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone

Product 1

HCID 21933988HCID 21933988, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred suspension of 2-(3-chlorophenyl)-4-tosyloxy-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone, prepared in Example 333, (0.0802 g, 0.15 mmol) in EtOH (1.5 mL) was added thiocresol (0.019 g, 0.15 mmol) and K2CO3 (0.0203 g, 0.15 mmol). The suspension was heated to 50° C. with stirring for 2.5 hours. The mixture was poured into H2O with constant stirring. The resulting precipitate was filtered, rinsed with H2O and dried to provide the desired product (yield: 0.060 g, 83%). mp 178-178° C. 1H NMR (300 MHz, DMSO d6) δ 2.19 (s, 3H), 3.23 (s, 3H), 6.95 (m, 2H), 7.08 (m, 2H), 7.52-7.66 (m, 3H), 7.72 (m, 1H), 7.88 (m, 2H), 8.08 (s, 1H). MS (DCI/NH3) m/z 483 (M+H)+, 500 (M+NH4)+. Anal. calc. for: C24H19ClN2O3S2.0.75H2O: C, 58.05; H, 4.16; N, 5.64. Found: C, 57.99; H, 3.69; N, 5.76.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washrinsed with H2O
  3. customdried

Sources & evidence

ORD record
ord-88601bfdf50140e094ebc66a050fcfc4
Source dataset
uspto-grants-2006_02
Patent number
US07001895B2

Reaction notes

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