Phosphorus oxychloride → HCID 68924249, compound

HRID 1788574Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:37]=[CH:36][C:9]2[N:10]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[NH:19][C:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][C:16]4=O)=[N:12][C:8]=2[CH:7]=1)=[O:5])[CH3:2].P(Cl)(Cl)([Cl:40])=O>>[CH2:1]([O:3][C:4]([C:6]1[CH:37]=[CH:36][C:9]2[N:10]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[N:19]=[C:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:17]=[C:16]4[Cl:40])=[N:12][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 86600381HCID 86600381, compound

Product 1

HCID 68924249HCID 68924249, compound

Conditions

Temperature: 100 °C

Procedure

1-Cyclohexyl-2-(4-oxo-2-phenyl-1,4-dihydro-quinolin-6-yl)-1H-benzoimidazole-5-carboxylic acid ethyl ester acid (4 g, 8.14 mmol) was dissolved in phosphorous oxy chloride and heated at 100° C. overnight. After evaporation of the solvent the product was recrystallized from methanol/water to give 3.96 g of crude product. Silica gel purification of the title compound proved to be unsatisfactory due to degradation of the product on the column. MS: 510.22 (M+H+).

Workup

customAfter evaporation of the solvent the product
customwas recrystallized from methanol/water

Sources & evidence

ORD record: ord-a3e64b83fe1941a496c990845a45cb8a
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511145B2

Reaction notes

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