Formic Acid → HCID 10812412, compound

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

Reactant 4

HCID 284Formic Acid

HCID 14798Sodium Hydroxide

HCID 31254N-Methylformamide

HCID 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).