Formic Acid → HCID 10812412, compound

HRID 1769187Notes

Reaction equation

HRID 1769187 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 (3×). The organic layer was washed with water (2×) 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 (3×)
  2. washThe organic layer was washed with water (2×) and brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d61d793dde7b466e8a305e297eaa547b
Source dataset
uspto-grants-1995_01
Patent number
US05380749

Reaction notes

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