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

HRID 2226203Notes

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

Participants

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

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

Sources & evidence

ORD record: ord-aa5cc61b26a542f2a341f9f17e238f0c
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05346917

Reaction notes

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