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

HRID 1769177Notes

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

Reaction notes

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