Sulfuric Acid → HCID 10815838, compound

Reaction equation

[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([CH2:13][C:14]#[N:15])[CH:10]=[CH:9][C:5]=1[C:6]([O-:8])=[O:7])[CH3:2].[CH:16]1([CH2:22][CH:23](O)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.S(=O)(=O)(O)[OH:38].Cl[C:43]1[CH:48]=CC=CC=1Cl>>[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([CH2:13][C:14]([NH:15][CH:23]([CH2:22][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:38])[CH:10]=[CH:9][C:5]=1[C:6]([O:8][CH2:48][CH3:43])=[O:7])[CH3:2]

Participants

Reactant 4

HCID 1118Sulfuric Acid

HCID 72391,2-Dichlorobenzene2×

HCID 21261766HCID 21261766, compound

HCID 54424526HCID 54424526, compound

Product 1

HCID 10815838HCID 10815838, compound

Procedure

At 23°-25° C., a solution of 2-ethoxy-4-cyanomethyl-benzoate (2.35 g, 10 mmol) and α-cyclohexylmethyl-2-piperidino-benzyl alcohol (2.88 g, 10 mmol) in o-dichlorobenzene (15 ml) is added dropwise to a mixture of concentrated sulphuric acid (15 ml) and o-dichlorobenzene (15 ml). The mixture is stirred for 2 hours at ambient temperature. The o-dichlorobenzene phase is then separated off and the residue is added to ice. After being made alkaline with soda solution, it is extracted with chloroform. The extracts are dried over sodium sulphate and concentrated by evaporation. The residue is purified by column chromatography on silica gel (toluene/acetone=10/1).