Ethanol → HCID 178469259, compound

HRID 1606540Notes

Reaction equation

HRID 1606540 reaction equation
[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][CH2:5][NH:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[C:11](Cl)[N:10]=[C:9]([CH3:17])[C:8]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(O)C.[S-2:27].[Na+].[Na+]>O>[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][CH2:5][NH:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[C:11]([SH:27])[N:10]=[C:9]([CH3:17])[C:8]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 702EthanolHCID 14804Sodium SulfideHCID 537171606-Chloro-4-[[3-(dimethylamino)propyl]amino]-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester

Product 1

HCID 178469259HCID 178469259, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

34.5 g. of 4-[[3-(dimethylamino)propyl]amino]-6-chloro-2-methyl-5-nitropyridine-3-carboxylic acid, ethyl ester are dissolved in 100 ml. of ethanol. 15 g. of sodium sulfide in 10 ml. of water are added and the mixture is stirred without cooling for 1 hour. After this time, the precipitated 4-[[3-(dimethylamino)propyl]amino]-6-mercapto-2-methyl-5-nitropyridine-3-carboxylic acid, ethyl ester is filtered off and recrystallized from methanol, yield 18 g. (53%), m.p. 131°-132°.

Workup

  1. temperaturewithout cooling for 1 hour
  2. filtrationAfter this time, the precipitated 4-[[3-(dimethylamino)propyl]amino]-6-mercapto-2-methyl-5-nitropyridine-3-carboxylic acid, ethyl ester is filtered off
  3. customrecrystallized from methanol, yield 18 g

Sources & evidence

ORD record
ord-46b50d976ae042f9a6e96f42efc24d34
Source dataset
uspto-grants-1976_04
Patent number
US03953461

Reaction notes

Loading…