Hydrochloric Acid → 2-Cyano-2-(3-phenoxy-phenylthiocarbamoyl)-acetamide

HRID 33757Notes

Reaction equation

HRID 33757 reaction equation
[OH-].[K+].[C:3]([CH2:5][C:6]([NH2:8])=[O:7])#[N:4].[O:9]([C:16]1[CH:17]=[C:18]([N:22]=[C:23]=[S:24])[CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>CN(C=O)C.O>[C:3]([CH:5]([C:23](=[S:24])[NH:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([O:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:17]=1)[C:6]([NH2:8])=[O:7])#[N:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7898CyanoacetamideHCID 14797Potassium HydroxideHCID 220412813-Phenoxyphenylisothiocyanate

Product 1

HCID 866073932-Cyano-2-(3-phenoxy-phenylthiocarbamoyl)-acetamideYield 72.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 85% powdered KOH in 20 ml DMF was added 1.74 g of cyanoacetamide at room temperature. The solution was stirred at room temperature for 15 minutes and then cooled in a water bath at room temperature. To this solution 4.7 g of 3-phenoxy-phenyl isothiocyanate was added dropwise. The solution exothermed slightly with the internal temperature rising to 28° C. during the addition. The solution was stirred at room temperature for 16 h, then diluted with 150 ml water and extracted with ethyl acetate to remove small amounts of starting material and by-products. The aqueous layer was isolated and acidified with 1N HCl to pH 1 with vigorous stirring. The resulting tan precipitate was filtered, washed with water, and dried for 16 hours in a vacuum oven to afford 4.66 g of 2-cyano-2-(3-phenoxy-phenylthiocarbamoyl)-acetamide.

Workup

  1. additionTo a suspension of 85%
  2. temperaturecooled in a water bath at room temperature
  3. additionrising to 28° C. during the addition
  4. stirringThe solution was stirred at room temperature for 16 h
  5. extractionextracted with ethyl acetate
  6. customto remove small amounts of starting material and by-products
  7. customThe aqueous layer was isolated
  8. filtrationThe resulting tan precipitate was filtered
  9. washwashed with water
  10. customdried for 16 hours in a vacuum oven

Sources & evidence

ORD record
ord-8308c8811e8c448395b0155e0af9b1c5
Source dataset
uspto-grants-2008_09
Patent number
US07429667B2

Reaction notes

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