Thionyl Chloride → HCID 57624577, compound

HRID 657589Notes

Reaction equation

HRID 657589 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:22]2[C:27](=[O:28])[NH:26][C:25](=[O:29])[C:24]([C:30]#[N:31])=[N:23]2)[CH:5]=[C:6]([Cl:21])[C:7]=1[O:8][C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12](=[O:18])[N:11]([CH2:19]O)[N:10]=1.S(Cl)([Cl:34])=O>O1CCCC1>[Cl:21][C:6]1[CH:5]=[C:4]([N:22]2[C:27](=[O:28])[NH:26][C:25](=[O:29])[C:24]([C:30]#[N:31])=[N:23]2)[CH:3]=[C:2]([Cl:1])[C:7]=1[O:8][C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12](=[O:18])[N:11]([CH2:19][Cl:34])[N:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 25230624HCID 25230624, compound

Product 1

HCID 57624577HCID 57624577, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-[3,5-dichloro-4-(1-hydroxymethyl-5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carbonitrile (600 mg, 1.29 mmol) in tetrahydrofuran (9.0 mL, 0.14 M) cooled to 0° C. was treated with thionyl chloride (0.28 mL, 3.84 mmol). The reaction mixture was allowed to slowly warm to 25° C. The reaction mixture was stirred at 25° C. overnight. At this time, the reaction mixture was concentrated in vacuo. The residue was taken up in benzene and was re-concentrated twice to afford 2-[3,5-dichloro-4-(1-chloromethyl-5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carbonitrile as a yellow solid. The material was used without further purification.

Workup

  1. concentrationAt this time, the reaction mixture was concentrated in vacuo
  2. concentrationwas re-concentrated twice

Sources & evidence

ORD record
ord-b77fc0ea1494458c98c26ff0d3827b33
Source dataset
uspto-grants-2011_12
Patent number
US08076334B2

Reaction notes

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