Sulfuric Acid → HCID 10815838, compound

HRID 1857021Notes

Reaction equation

HRID 1857021 reaction equation
[CH2:1]([O:3][C:4]1[CH:14]=[C:13]([CH2:15][C:16]#[N:17])[CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[CH:18]1([CH2:24][CH:25](O)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.S(=O)(=O)(O)[OH:40]>ClC1C=CC=CC=1Cl>[CH2:1]([O:3][C:4]1[CH:14]=[C:13]([CH2:15][C:16]([NH:17][CH:25]([CH2:24][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[O:40])[CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10489807Benzoic acid, 4-(cyanomethyl)-2-ethoxy-, ethyl esterHCID 54424526HCID 54424526, compound

Product 1

HCID 10815838HCID 10815838, compound

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent2×

Procedure

At 23-25° C., a solution of ethyl 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).

Workup

  1. customThe o-dichlorobenzene phase is then separated off
  2. additionthe residue is added to ice
  3. extractionis extracted with chloroform
  4. dry with materialThe extracts are dried over sodium sulphate
  5. concentrationconcentrated by evaporation
  6. customThe residue is purified by column chromatography on silica gel (toluene/acetone=10/1)

Sources & evidence

ORD record
ord-fdc29c0be4fc4621bf299119242b67ac
Source dataset
uspto-grants-2000_11
Patent number
US06143769

Reaction notes

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