Sodium Hydroxide → HCID 20313862, compound

HRID 2419555Notes

Reaction equation

HRID 2419555 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][C:13]([O:15]CC)=[O:14].[OH-].[Na+]>C(O)C.O>[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][C:13]([OH:15])=[O:14]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86735879HCID 86735879, compound

Product 1

HCID 20313862HCID 20313862, compoundYield 70.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-[(1,3-benzodithiol-2ylidene)amino]-propanoic acid, ethyl ester (3.0g, prepared as described in Example 2) and sodium hydroxide (499 mg) in 120 ml of absolute ethanol is stirred at room temperature for 120 hours. The reaction mixture is concentrated in vacuo, and the resultant solid residue is washed with diethyl ether to remove unreacted starting material. The crude reaction product is dissolved in 50 ml of water, filtered through Celite, and the aqueous solution is then treated with 10% hydrochloric acid until the pH is 5. The resultant precipitate is collected by filtration and dried in vacuo at 60° C overnight. Recrystallization of the dried product from n-pentyl alcohol yields 1.9g of the title compound, melting point 203-204° C.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. washthe resultant solid residue is washed with diethyl ether
  3. customto remove unreacted
  4. customThe crude reaction product
  5. filtrationfiltered through Celite
  6. additionthe aqueous solution is then treated with 10% hydrochloric acid until the pH is 5
  7. filtrationThe resultant precipitate is collected by filtration
  8. customdried in vacuo at 60° C overnight
  9. customRecrystallization of the dried product from n-pentyl alcohol

Sources & evidence

ORD record
ord-b07ddbee47df4532a2548995be9b820f
Source dataset
uspto-grants-1978_08
Patent number
US04107175

Reaction notes

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