Formic Acid → HCID 10812412, compound

HRID 1377792Notes

Reaction equation

HRID 1377792 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 sovlent 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 sovlent was removed in vacuo

Sources & evidence

ORD record
ord-a42fd46d5dc14c3eada410b004cfa759
Source dataset
uspto-grants-1997_09
Patent number
US05665760

Reaction notes

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