Triethyl ethane-1,1,2-tricarboxylate → HCID 178470755, compound

HRID 968213Notes

Reaction equation

HRID 968213 reaction equation
[O-]CC.[Na+].[NH2:5][C:6]([NH2:8])=[S:7].[CH:9]([C:21](OCC)=[O:22])([C:16](OCC)=[O:17])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]>>[OH:22][C:21]1[C:9]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:16]([OH:17])[N:8]=[C:6]([SH:7])[N:5]=1

Participants

4

Reactant 3

HCID 81961Triethyl ethane-1,1,2-tricarboxylateHCID 2723790ThioureaHCID 2723922Sodium ethoxide

Product 1

HCID 178470755HCID 178470755, compoundYield 51%

Procedure

To a solution of sodium ethoxide [prepared from sodium metal (1.6 g) and ethanol] was added thiourea (5.28 g) and triethyl 1,1,2-ethane tricarboxylate (17 g). The mixture was heated under reflux for 8 hours. The solution was cooled to room temperature and the solid collected by filtration, washed with a little ether. The solid was dissolved in water (100 ml) and the pH adjusted to 6-7 by the addition of hydrochloric acid. No solid was precipitated therefore the solution was lyophilised to give a pink solid (8.1 g)

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 8 hours
  3. filtrationthe solid collected by filtration
  4. washwashed with a little ether
  5. dissolutionThe solid was dissolved in water (100 ml)
  6. additionthe pH adjusted to 6-7 by the addition of hydrochloric acid
  7. customNo solid was precipitated

Sources & evidence

ORD record
ord-df1ed3cdba7a4e1994915b332ba934e8
Source dataset
uspto-grants-2005_10
Patent number
US06958344B2

Reaction notes

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