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

HRID 1769178Notes

Reaction equation

HRID 1769178 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

4

Reactant 1

HCID 3334581-(2-Dimethylaminoethylamino)-4-(hydroxymethyl)thioxanthen-9-one

Product 1

HCID 22915308HCID 22915308, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 1140TolueneSolvent

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

  1. temperaturethe mixture was heated at 60° C. for 1 hour
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9cf7cc4b742d40b5bfaced681d1cfc1b
Source dataset
uspto-grants-1995_01
Patent number
US05380749

Reaction notes

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