Formic Acid → HCID 10812412, compound

HRID 2226213Notes

Reaction equation

HRID 2226213 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[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](C=O)=[CH:9][CH:8]=1)[CH3:2].[CH:28]([OH:30])=O.[OH-].[Na+].[CH3:33][NH:34][CH:35]=O>>[CH2:1]([N:3]([CH2:26][CH3:27])[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]([CH2:33][N:34]([CH3:35])[CH:28]=[O:30])=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 4

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 31254N-MethylformamideHCID 13504755HCID 13504755, compound

Product 1

HCID 10812412HCID 10812412, compoundYield 89.9%

Procedure

A solution of 1-[[2-(diethylamino)ethyl]amino]-7-methoxy-9-oxothioxanthen-4-carboxaldehyde (3 g, 7.8 mmol) and 1.5 mL of formic acid in 25.5 mL of N-methylformamide was heated to 170° C. for 8 h with stirring under nitrogen. The reaction mixture was poured into 160 mL of ice/water, basified with 35% of NaOH solution, and extracted into chloroform (3x). The organic layer was washed with water (2x) and brine, dried over sodium sulfate, and the solvent was removed in vacuo affording 3 g (89.9 %) of the desired N-[[1-[[2-(diethylamino)ethyl]amino]-7-methoxy-9-oxothioxanthen-4-yl]methyl]-N-methylformamide (Formula IV: R1 =R2 =Et; R4 =Me; R8 =7-OCH3 ; n=2).

Workup

  1. extractionextracted into chloroform (3x)
  2. washThe organic layer was washed with water (2x) and brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e8593376e71d4104b303b7208d63d995
Source dataset
uspto-grants-1994_09
Patent number
US05346917

Reaction notes

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