p-Toluenesulfonic acid → HCID 70432804, compound

HRID 1905713Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH2:19][O:20][CH2:21][CH2:22][NH:23][CH3:24])=[C:9]1[C:25]([O:27][CH2:28][CH3:29])=[O:26].[C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[N:38]=[C:39](OCC)[CH3:40])#[N:31].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH2:19][O:20][CH2:21][CH2:22][N:23]([CH3:24])[C:39](=[N:38][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[C:30]#[N:31])[CH3:40])=[C:9]1[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-(2-methylaminoethoxymethyl)-1,4-dihydropyridine (2.5 g.), ethyl N-(2-cyanophenyl)acetimidate (1.1 g.) and p-toluenesulphonic acid (0.1 g.) was heated at 150° C. for 4 hours, cooled, and then dissolved in chloroform. The solution was washed with sodium bicarbonate solution, water and dried over sodium sulphate. Evaporation of the solvent gave an oil which was chromatographed on silica gel. Elution with chloroform/hexane (1:1) gave the product as an oil (0.95 g.) which was used directly in the next stage.

Workup

temperaturecooled
washThe solution was washed with sodium bicarbonate solution, water
dry with materialdried over sodium sulphate
customEvaporation of the solvent
customgave an oil which
customwas chromatographed on silica gel
washElution with chloroform/hexane (1:1)

Sources & evidence

ORD record: ord-dc5b45bc72d24840a5c77e46eade6e39
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04647565

Reaction notes

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