Sodium Hydroxide → HCID 19696466, compound

HRID 863462Notes

Reaction equation

HRID 863462 reaction equation
[C:1]1([CH2:7][N:8]([CH3:29])[CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18](=[S:28])[NH:19]C(=O)C3C=CC=CC=3)=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>O>[C:1]1([CH2:7][N:8]([CH3:29])[CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([NH:17][C:18]([NH2:19])=[S:28])=[CH:15][CH:16]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19696464HCID 19696464, compound

Product 1

HCID 19696466HCID 19696466, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-(4-(2-(benzylmethylamino)ethyl)phenyl)-1-benzoyl-2-thiourea (step (e), 2.4 g, 5.95 mmol) and 2.5N aqueous sodium hydroxide (20 ml) was heated at 90° C. for 35 minutes with stirring. The warm reaction mixture was then poured into water (60 ml) with stirring. The product was extracted into three portions of methylene chloride. The combined extracts were washed with water, dried over magnesium sulfate and concentrated to dryness to yield 1.71 g of crude 1-(4-(2-((phenylmethyl)(methyl)amino)ethyl)phenyl)-2-thiourea. The product was crystallized from benzene, m.p. 119°-21.5° C.

Workup

  1. customThe warm reaction mixture
  2. stirringwith stirring
  3. extractionThe product was extracted into three portions of methylene chloride
  4. washThe combined extracts were washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-723a9f48befd40978d24f08f4abccbe1
Source dataset
uspto-grants-1998_02
Patent number
US05721247

Reaction notes

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