Phosphorus oxychloride → HCID 57468674, compound

HRID 1927848Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[C:13]([CH3:15])[NH:12][C:11](=O)[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:11]1[CH:10]=[C:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH:14]=[C:13]([CH3:15])[N:12]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 57468675HCID 57468675, compound

Product 1

HCID 57468674HCID 57468674, compound

Procedure

4-(3,4-Dichloro-phenyl)-6-methyl-1H-pyridin-2-one: The compound was prepared from the above described (E)-4-(3,4-dichloro-phenyl)-but-3-en-2-one (26.7 g, 124 mmol), commercially available 1-ethoxycarbonylmethyl-pyridinium bromide [CAS-No. 17282-40-5] (33.6 g, 137 mmol) and ammonium acetate (47.8 g, 621 mmol) in EtOH (150 mL) according to general procedure Ib step 1. Obtained as a light brown solid (25.4 g, 81%). MS (ISP) 254.1 [(M+H)+], 256.2 [(M+2+H)+] and 258.0 [(M+4+H)+]0.3) The title compound was prepared from the above described 4-(3,4-dichloro-phenyl)-6-methyl-1H-pyridin-2-one (25.4 g, 100 mmol) and phosphoryl chloride (45.6 mL, 500 mmol) according to the general procedure Ia to d preparation of chlorides. Obtained as an off-white solid (23.7 g, 87%). MS (ISP) 272.1 [(M+H)+], 274.0 [(M+2+H)+], 276.0 [(M+4+H)+] and 278.0 [(M+6+H)+].

Sources & evidence

ORD record: ord-d7148ed7d41e4a388a7a79905d303fb8
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183262B2

Reaction notes

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