Water → HCID 21933988, compound

HRID 1241799Notes

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

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: C24H19ClN2O3S2.0.75 H2O: C, 58.05; H, 4.16; N, 5.64. Found: C, 57.99; H, 3.69; N, 5.76.

Workup

filtrationThe resulting precipitate was filtered
washrinsed with H2O
customdried

Sources & evidence

ORD record: ord-3ef8b95665954c62a79e99621a1204ef
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115591B2

Reaction notes

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