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

HRID 2226218Notes

Reaction equation

HRID 2226218 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]([CH:22]=O)=[CH:9][CH:8]=1)[CH3:2].[CH:26]([NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27].C(O)=O>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]([CH2:22][N:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:26]=[O:27])=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7671FormanilideHCID 987989H-Thioxanthene-4-carboxaldehyde, 1-[[2-(diethylamino)ethyl]amino]-9-oxo-

Product 1

HCID 10742600N-[[1-[[2-(Diethylamino)ethyl]amino]-9-oxothioxanthen-4-yl]methyl]-N-phenyl formamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1-[[2-(diethylamino)ethyl]amino]-9-oxothioxanthen-4-carboxaldehyde (3.40 g, 9.59 mmol), formanilide (31g) and formic acid (3 mL) were heated to 160° C. for 2 hours. The mixture was cooled, poured into water (200 mL) and extracted with ether (3×150 mL). The aqueous layer was basified with 5N NaOH, extracted with CHCl3 (3×150 mL) and the combined organic extracts were dried over Na2SO4 and filtered through florisil eluting with CHCl3 (100%), then 5% isopropylamine/CHCl3. The solvent was removed in vacuo and the residue was purified by column chromatography on silica eluting with 0.5% to 1% isopropylamine/CHCl3 and then by recrystallization from benzene/hexane (2x) to afford 1.88 g of the desired product.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ether (3×150 mL)
  3. extractionextracted with CHCl3 (3×150 mL)
  4. dry with materialthe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered through florisil eluting with CHCl3 (100%)
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by column chromatography on silica eluting with 0.5% to 1% isopropylamine/CHCl3
  8. customby recrystallization from benzene/hexane (2x)

Sources & evidence

ORD record
ord-c7d45b7f141641a58a292e9985a00c7d
Source dataset
uspto-grants-1994_09
Patent number
US05346917

Reaction notes

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