Formic Acid → N-[[1-[[2-(Diethylamino)ethyl]amino]-9-oxothioxanthen-4-yl]methyl]-N-ethylformamide

HRID 2226199Notes

Reaction equation

HRID 2226199 reaction equation
[CH2:1]([N:3]([CH2:24][CH3:25])[CH2:4][CH2:5][NH:6][C:7]1[C:20]2[C:19](=[O:21])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[S:12][C:11]=2[C:10](C=O)=[CH:9][CH:8]=1)[CH3:2].[CH2:26]([NH:28][CH:29]=[O:30])[CH3:27].[CH:31](O)=O.[OH-].[Na+]>O>[CH2:1]([N:3]([CH2:24][CH3:25])[CH2:4][CH2:5][NH:6][C:7]1[C:20]2[C:19](=[O:21])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[S:12][C:11]=2[C:10]([CH2:31][N:28]([CH2:26][CH3:27])[CH:29]=[O:30])=[CH:9][CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 12319EthylformamideHCID 14798Sodium HydroxideHCID 987989H-Thioxanthene-4-carboxaldehyde, 1-[[2-(diethylamino)ethyl]amino]-9-oxo-

Product 1

HCID 11795910N-[[1-[[2-(Diethylamino)ethyl]amino]-9-oxothioxanthen-4-yl]methyl]-N-ethylformamideYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2.0 g (5.6 mmol) of 1-[[2-(diethylamino)ethyl]amino]-9-oxo-thioxanthen-4-carboxaldehyde, N-ethylformamide (24.0 mL) and formic acid (3.0 mL, 79.5 mmol) was heated at 170° C. for 4 hours. The reaction mixture was cooled, poured into water and made basic with 10% sodium hydroxide. A solid was obtained which was collected by filtration and washed with water. The solid residue was taken up in chloroform/water, and the organic layer was separated and dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by radial chromatography eluting with isopropylamine/methanol/ethyl acetate (0.5/1/98.5) to afford 1.32 g (57%) of the N-ethylformamide as an orange solid, m.p.75°-77° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customA solid was obtained which
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customthe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by radial chromatography
  9. washeluting with isopropylamine/methanol/ethyl acetate (0.5/1/98.5)

Sources & evidence

ORD record
ord-16550a3e719a408c98861a8325aa4704
Source dataset
uspto-grants-1994_09
Patent number
US05346917

Reaction notes

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