Acetic Acid → HCID 11303733, compound

HRID 1719363Notes

Reaction equation

HRID 1719363 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]=[C:16]([O:22][CH3:23])[CH:17]=3)[S:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH3:2].[C:26](O)(=[O:28])C.[OH-].[Na+].C(Cl)(Cl)Cl.CO>C=O.C(Cl)(Cl)Cl>[CH2:24]([N:3]([CH2:1][CH3:2])[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]=[C:16]([O:22][CH3:23])[CH:17]=3)[S:12][C:11]=2[C:10]([CH2:26][OH:28])=[CH:9][CH:8]=1)[CH3:25]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 21584188Chloroform methanolHCID 22915306HCID 22915306, compound

Product 1

HCID 11303733HCID 11303733, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 712FormaldehydeSolventHCID 6212ChloroformSolvent

Procedure

A solution of 2.70 g (7.5 mmol) of 1-[[2-(Diethylamino)ethyl]amino]-7-methoxy-9H-thioxanthen-9-one in 135 ml of 37% formalin containing 2.7 ml of N acetic acid was heated on the steam bath for 4 hr, cooled and made alkaline with 10N NaOH solution. The suspension was taken up in CHCl3. The extract was evaporated to dryness and covered with CHCl3. The extract was evaporated to dryness and covered with C2H5OH. The "dimer" separated: yield 400 mg. It was recrystallized from 2-methoxy-ethanol. The filtrate was evaporated to dryness to leave an oil, which, after chromatography on silica gel with CHCl3 -CH3OH as the eluant, furnished 1.30 g (44.5%) of the desired product, mp 103°-105° C. after crystallization from ethyl acetate-petroleum ether.

Workup

  1. temperaturecooled
  2. customThe extract was evaporated to dryness
  3. customThe extract was evaporated to dryness
  4. customThe "dimer" separated
  5. customIt was recrystallized from 2-methoxy-ethanol
  6. customThe filtrate was evaporated to dryness
  7. customto leave an oil, which

Sources & evidence

ORD record
ord-0de0da04255341fabcbc44ac21c2cb5e
Source dataset
uspto-grants-1985_09
Patent number
US04539412

Reaction notes

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