Hydrochloric Acid → HCID 23461732, compound

HRID 2286590Notes

Reaction equation

HRID 2286590 reaction equation
[C:1]1([C:7]2[NH:8][C:9]([S:18][C:19]#N)=[CH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CI.[OH-].[K+].Cl>CO.O>[C:12]1([C:11]2[CH:10]=[C:9]([S:18][CH3:19])[NH:8][C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 15572344HCID 15572344, compound

Product 1

HCID 23461732HCID 23461732, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 1.4 g (0.005 mole) 2,3-diphenyl-5-thiocyanatopyrrole, 0.85 g (0.006 mole) methyl iodide in 10 ml methanol was added dropwise at 0° a solution of 0.8 g (~0.012 mole, 85%) potassium hydroxide in 5 ml water+5 ml methanol. The mixture was allowed to warm to room temperature, then was poured into 100 ml ice water and neutralized with hydrochloric acid. The aqueous mixture was extracted with methylene chloride, and the extracts dried and concentrated. The residue was chromatographed on 50 g Silic AR CC-7, eluting with toluene to give 1.2 g (90%) yellow oil.

Workup

  1. extractionThe aqueous mixture was extracted with methylene chloride
  2. customthe extracts dried
  3. concentrationconcentrated
  4. customThe residue was chromatographed on 50 g Silic AR CC-7
  5. washeluting with toluene

Sources & evidence

ORD record
ord-18ab3b1eb1d54ca99042153a2852086a
Source dataset
uspto-grants-1981_05
Patent number
US04267184

Reaction notes

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