Formic Acid → HCID 10667694, compound

HRID 1769176Notes

Reaction equation

HRID 1769176 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[CH2:4][CH2:5][CH2:6][NH:7][C:8]1[C:21]2[C:20](=[O:22])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[S:13][C:12]=2[C:11]([CH:23]=O)=[CH:10][CH:9]=1)[CH3:2].C(O)=O.[OH-].[Na+].[CH3:32][NH:33]C=O>>[CH2:1]([N:3]([CH2:25][CH3:26])[CH2:4][CH2:5][CH2:6][NH:7][C:8]1[C:21]2[C:20](=[O:22])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[S:13][C:12]=2[C:11]([CH2:23][NH:33][CH3:32])=[CH:10][CH:9]=1)[CH3:2]

Participants

5

Reactant 4

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 31254N-MethylformamideHCID 22915315HCID 22915315, compound

Product 1

HCID 10667694HCID 10667694, compound

Procedure

A solution of 1-[[3-(diethylamino)propyl]amino]-9-oxothioxanthen-4-carboxaldehyde (3.3 g, 8.96 mmol) and 3 g of formic acid in 50 mL of N-methylformamide was allowed to reflux for 2 h. The mixture was basified with 5 mL of a 5N sodium hydroxide solution and extracted into chloroform (3×150ml). The organic layer was dried over sodium sulfate, concentrated in vacuo, and a crude oil was dissolved in a 3N aqueous HCl solution (50 ml) and heated on a steam bath for 3 h. The above mixture was cooled, basified with 30 mL of 35% NaOH, extracted into chloroform (3×150ml), the organic layer dried over sodium sulfate and concentrated in vacuo to afford a brown oil. The brown oil was purified by flash chromatography (silica gel; 5% triethylamine/Et2O, then 5% Et3N/EtOAc, then triethylamine/methanol/EtOAc (5:5:90)) to afford 1.1 g of 1-[[3-(diethylamino)propyl]amino]-4-(methylaminomethyl)thioxanthen-9-one, as a clear orange gum. The above gum was converted into the corresponding dihydrochloride by treatment with 6N HCl in ether to afford 1.04 g of the dihydrochloride.3/2 hydrate as a yellow powder, m.p. 222°-224° C.

Workup

  1. temperatureto reflux for 2 h
  2. extractionextracted into chloroform (3×150ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutiona crude oil was dissolved in a 3N aqueous HCl solution (50 ml)
  6. temperatureheated on a steam bath for 3 h
  7. temperatureThe above mixture was cooled
  8. extractionextracted into chloroform (3×150ml)
  9. dry with materialthe organic layer dried over sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customto afford a brown oil
  12. customThe brown oil was purified by flash chromatography (silica gel

Sources & evidence

ORD record
ord-09e9cc948360467e9e64e33e155624d7
Source dataset
uspto-grants-1995_01
Patent number
US05380749

Reaction notes

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