Potassium Hydroxide → HCID 20313838, compound

HRID 2419554Notes

Reaction equation

HRID 2419554 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][C:12]([O:14]CC)=[O:13].[OH-].[K+]>CO>[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][C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 12494980HCID 12494980, compound

Product 1

HCID 20313838HCID 20313838, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [(1,3-benzodithiol-2-ylidene) amino]-acetic acid ethyl ester (2.5g, prepared as described in Example 1) and potassium hydroxide (550 mg) in 500 ml of anhydrous methyl alcohol is stirred at room temperature for 120 hours. The reaction mixture is then concentrated in vacuo. The resultant solid residue is triturated with diethyl either to remove unreacted starting material. The undissolved residue is then dissolved in 50 ml of water and filtered through Celite. The aqueous solution is treated with 10% hydrochloric acid until the pH is 5. The resultant precipitate is collected by filtration and dried in vacuo over phosphorous pentoxide at 60° C for about 16 hours. The dried solid is recrystallized twice from ethyl acetate to yield 1.3g of the title compound, melting point 195°-200° C.

Workup

  1. concentrationThe reaction mixture is then concentrated in vacuo
  2. customThe resultant solid residue is triturated with diethyl
  3. customto remove unreacted
  4. dissolutionThe undissolved residue is then dissolved in 50 ml of water
  5. filtrationfiltered through Celite
  6. additionThe aqueous solution is treated with 10% hydrochloric acid until the pH is 5
  7. filtrationThe resultant precipitate is collected by filtration
  8. dry with materialdried in vacuo over phosphorous pentoxide at 60° C for about 16 hours
  9. customThe dried solid is recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-c1cdf8c253f34548b359a9b9fb4ce617
Source dataset
uspto-grants-1978_08
Patent number
US04107175

Reaction notes

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