Ethanol → HCID 20313833, compound

HRID 2419131Notes

Reaction equation

HRID 2419131 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[S:3][C:2]1=[N:10][CH2:11][CH2:12][CH2:13]C(OCC)=O.[OH-:19].[Na+].[CH2:21]([OH:23])C>>[S:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][C:2]1=[N:10][CH:11]([CH2:12][CH3:13])[C:21]([OH:23])=[O:19]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 85939525HCID 85939525, compound

Product 1

HCID 20313833HCID 20313833, compound

Procedure

A solution of 4-[(1,3-benzodithiol-2-ylidene)amino]butanoic acid, ethyl ester (3g, prepared as described in Example 5) and sodium hydroxide (427 mg) in 80% aqueous ethanol (50 ml) is stirred at room temperature for seven days. The reaction mixture is concentrated in vacuo and the residue triturated with two 50 ml portions of hot benzene. The solid residue is dissolved in 100 ml of water, filtered through Celite, and the filtrate treated with 10% hydrochloric acid until the pH is 4. The solid precipitate is collected by filtration and washed on the filter with water. Recrystallization of the solid product from chloroform yields 1.3g of the title compound, melting point 140°-142° C.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe residue triturated with two 50 ml portions of hot benzene
  3. dissolutionThe solid residue is dissolved in 100 ml of water
  4. filtrationfiltered through Celite
  5. additionthe filtrate treated with 10% hydrochloric acid until the pH is 4
  6. filtrationThe solid precipitate is collected by filtration
  7. washwashed on the
  8. filtrationfilter with water
  9. customRecrystallization of the solid product from chloroform

Sources & evidence

ORD record
ord-3aaa3aff9f674270b58d7d85b4482076
Source dataset
uspto-grants-1978_08
Patent number
US04104467

Reaction notes

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