Ammonia → 2-(3-Chloro-4-fluorophenyl)-4-(4-chlorophenyl)-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone

Participants

Role	Name	HCID	Charge
Reactant	Ammonia	HCID 222	—
Reactant	4-Bromo-2-chloro-1-fluorobenzene	HCID 3543065	—
Reactant	4-(4-chlorophenyl)-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone	HCID 21934129	—
Product	2-(3-Chloro-4-fluorophenyl)-4-(4-chlorophenyl)-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone	HCID 10117198	—

Reaction Steps

The title compound was prepared according to Example 93, starting with 4-(4-chlorophenyl)-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone (described in Example 99) in place of 4-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone and substituting 1-bromo-3-chloro-4-fluorobenzene in place of 4-bromothioanisole (yield: 330 mg, 58.8%). mp 205° C. 1H NMR (300 MHz, CDCl3) δ 3.10 (s, 3H), 7.17 (d, J=9 Hz, 2H), 7.23-7.31 (m, 1H), 7.28 (d, J=9 Hz, 2H), 7.41 (d, J=9 Hz, 2H), 7.65 (ddd, J=9 Hz, 3 Hz, 1.5 Hz, 1H), 7.85 (dd, J=9 Hz, 3 Hz, 1H), 7.93 (d, J=9 Hz, 2H), 8.01 (s, 1H). MS (DCI/NH3) m/z 489 (M+H)+, 508 (M+NH4)+. Anal. calc. for C23H15Cl2N2O3S: C,56.44; H, 3.17; N, 5.73. Found: C, 56.37; H, 3.19; N, 5.64.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06307047B1
Source dataset	uspto-grants-2001_10
ORD ID	ord-a29fb60deaf342d4ae5aa5f8e49a9a18
Source note	uspto-grants-2001_10