Hydrochloric Acid → HCID 20259029, compound

HRID 1583543Notes

Reaction equation

HRID 1583543 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([C:9]2[NH:10][C:11](=[O:15])[NH:12][C:13]=2[CH3:14])=[O:8])=[CH:4][CH:3]=1.[CH3:16][N:17](C)C=O.Cl>O>[C:16]([C:2]1[S:6][C:5]([C:7]([C:9]2[NH:10][C:11](=[O:15])[NH:12][C:13]=2[CH3:14])=[O:8])=[CH:4][CH:3]=1)#[N:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 20259032HCID 20259032, compound

Product 1

HCID 20259029HCID 20259029, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 4-[(5-bromo-2-thienyl)carbonyl]-5-methyl-1,3-dihydro-2H-imidazol-2-one (10 grams, 0.034 mole), cuprous cyanide (3.0 grams, 0.034 mole) and dimethylformamide (150 ml) are refluxed for 4 hours. The resulting mixture is poured into a solution of 200 grams ferric chloride and 50 ml concentrated hydrochloric acid in 300 ml water. After the reaction mixture is maintained at 60°-70° C. for 20 minutes, the layers were separated. The aqueous layer is extracted with toluene and the combined organic layers are washed with water and dried. Evaporation of solvent gives the title compound which is recrystallized from methanol.

Workup

  1. temperatureare refluxed for 4 hours
  2. temperatureAfter the reaction mixture is maintained at 60°-70° C. for 20 minutes
  3. customthe layers were separated
  4. extractionThe aqueous layer is extracted with toluene
  5. washthe combined organic layers are washed with water
  6. customdried
  7. customEvaporation of solvent

Sources & evidence

ORD record
ord-457fc9c8d9e644f1895f7a5223e03419
Source dataset
uspto-grants-1985_11
Patent number
US04552880

Reaction notes

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