Potassium Iodide → HCID 14233447, compound

HRID 2073948Notes

Reaction equation

HRID 2073948 reaction equation
[OH-].[K+].[NH2:3][C:4]1[CH:13]=[CH:12][C:11]([S:14][C:15]#N)=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7].[CH2:17](Br)C.[I-].[K+]>CO>[NH2:3][C:4]1[CH:13]=[CH:12][C:11]([S:14][CH2:15][CH3:17])=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6332Ethyl BromideHCID 14797Potassium HydroxideHCID 799394Methyl 2-amino-5-thiocyanatobenzoate

Product 1

HCID 14233447HCID 14233447, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
10 °C

Procedure

To a 500 ml flask fitted with a magnetic stirrer, dropping funnel and thermometer, and containing a solution of 12.7 g (0.192 mol) of 85% potassium hydroxide in 300 ml of methanol was added in portions 10.0 g (0.0481 mol) of methyl 2-amino-5-thiocyanatobenzoate. The solution was cooled to 10° C. and a solution of 6.29 g (0.058 mol) ethylbromide in 50 ml of methanol was added over 10 minutes. This was followed by the addition of 8.0 g (0.048 mol) potassium iodide. After 2.5 hours, the reaction mixture was evaporated to a semi-solid under reduced pressure and treated with 300 ml of water. The aqueous solution was extracted with chloroform, and the organic layer dried over magnesium sulfate. The solution was filtered and evaporated to give 7.5 g (79%) of crude product. This material was recrystallized from hexane to give 3.01 g (32%) of the title compound, m.p. 97°-100° C.

Workup

  1. customTo a 500 ml flask fitted with a magnetic stirrer
  2. customthe reaction mixture was evaporated to a semi-solid under reduced pressure
  3. additiontreated with 300 ml of water
  4. extractionThe aqueous solution was extracted with chloroform
  5. dry with materialthe organic layer dried over magnesium sulfate
  6. filtrationThe solution was filtered
  7. customevaporated
  8. customto give 7.5 g (79%) of crude product
  9. customThis material was recrystallized from hexane

Sources & evidence

ORD record
ord-715cf5cff6f04695b50ef306def079c3
Source dataset
uspto-grants-1990_04
Patent number
US04920224

Reaction notes

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