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Formaldehyde → 1-(2-Dimethylaminoethylamino)-4-(hydroxymethyl)thioxanthen-9-one

HRID 1769177
Notes
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Reaction equation

HRID 1769177 reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][NH:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[S:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[CH2:22]=[O:23].[OH-].[Na+]>C(O)(=O)C>[CH:6]([NH2:5])([CH3:19])[CH3:7].[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][NH:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[S:11][C:10]=2[C:9]([CH2:22][OH:23])=[CH:8][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 18947267HCID 18947267, compound

Product 2

HCID 6363IsopropylamineHCID 3334581-(2-Dimethylaminoethylamino)-4-(hydroxymethyl)thioxanthen-9-oneYield 64%

Reagents, catalysts & solvents 1

HCID 176
Acetic Acid
Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-[[2-(dimethylamino)ethyl]amino]thioxanthen-9-one (13 g, 0.044 mol) , 37% formalin (390 mL) and 5N acetic acid (6.5 mL) was heated to 100° C. for 8.5 hours, allowed to stand over the weekend and then was heated at 100° C. for several more hours. The mixture was poured into ice water, basified with 35% NaOH and extracted with chloroform. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica eluting in succession with; 25% CHCL3 /hexane; 50% CHCl3 /hexane; 75% CHCl3 /hexane; 100% CHCl3 ; 0.5% isopropylamine/chloroform; 1% isopropylamine/chloroform; 2% isopropylamine/chloroform; then 2% isopropylamine/2% MeOH/CHCl3 to afford 9.2 g (64%) of 1-[[2-(dimethylamino) ethyl]amino]-4-(hydroxymethyl)thioxanthen-9-one.

Workup

  1. temperaturewas heated at 100° C. for several more hours
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica eluting in succession with

Sources & evidence

ORD record
ord-fabb44c712d948a49041b24ae75c900f
Source dataset
uspto-grants-1995_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05380749

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes