Triethylamine → HCID 178519758, compound

HRID 2255363Notes

Reaction equation

HRID 2255363 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[CH:3][C:2]=1[C:10]([OH:12])=O.[S:13](Cl)(Cl)=O.[NH:17]1[CH2:22][CH2:21][S:20][CH2:19][CH2:18]1.[CH2:23]([N:25](CC)[CH2:26][CH3:27])[CH3:24]>C1(C)C=CC=CC=1.CN(C)C=O>[NH:17]1[CH2:22][CH2:21][SH:20]([C:10]([C:2]2[CH:3]=[C:4]([C:7]([SH:13]3[CH2:27][CH2:26][NH:25][CH2:23][CH2:24]3)=[O:9])[CH:5]=[CH:6][N:1]=2)=[O:12])[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 103652,4-Pyridinedicarboxylic acidHCID 24386Thionyl ChlorideHCID 67164Thiomorpholine

Product 1

HCID 178519758HCID 178519758, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

5 g (0.03 mol) of pyridine-2,4-dicarboxylic acid are suspended in 100 ml of toluene. 4.4 ml (0.06 mol) of thionyl chloride +1 ml of dimethylformamide are added dropwise at room temperature. The mixture is boiled under reflux for 2 hours until the resulting evolution of gas has ended and the solution has become clear. It is cooled to 0° C. and a solution of 60 ml (0.06 mol) of thiomorpholine and 10.4 ml (0.075 mol) of triethylamine in 20 ml of toluene is added dropwise.

Workup

  1. temperatureunder reflux for 2 hours until the resulting evolution of gas

Sources & evidence

ORD record
ord-17bb38e9a848448699fcd24929d5136c
Source dataset
uspto-grants-1993_08
Patent number
US05240921

Reaction notes

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