1-(2-Dimethylaminoethylamino)-4-(hydroxymethyl)thioxanthen-9-one → HCID 22915308, compound

HRID 2226204Notes

Reaction equation

[CH3:1][N:2]([CH3:23])[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]([CH2:21][OH:22])=[CH:8][CH:7]=1>C1(C)C=CC=CC=1.[O-2].[Mn+2]>[CH3:1][N:2]([CH3:23])[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]([CH:21]=[O:22])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-[[2-(dimethylamino)ethyl]amino]-4-(hydroxymethyl)thioxanthen-9-one (9.2 g, 0.028 mol) in toluene (322 mL) was heated to about 60 'C. and then manganese oxide (MnO2, 16 g) was added and the mixture was heated at 60° C. for 1 hour. The mixture was filtered and the filtrate was concentrated in vacuo to afford 7.9 g (87%) of 1-[[2-(dimethylamino)ethyl]amino]-9-oxothioxanthen-4-carboxaldehyde (Formula II: R1 =R2 =Me; R8 =H; n=2).

Workup

temperaturewas heated to about 60 'C
filtrationThe mixture was filtered
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-ef35c0cc35c44a20b66a52814246b0fa
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05346917

Reaction notes

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