Thiocyanic acid, chloromethyl ester → HCID 54225945, compound

HRID 2049668Notes

Reaction equation

HRID 2049668 reaction equation
[K].[C:2]([OH:10])(=[S:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:11][CH2:12]SC#N>CO>[Cl:11][CH2:12][O:10][C:2](=[S:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 76755Thiocyanic acid, chloromethyl esterHCID 5462222PotassiumHCID 178526132HCID 178526132, compound

Product 1

HCID 54225945HCID 54225945, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

28 g (0.16 mol) of the potassium salt of thiobenzoic acid were dissolved in 550 ml of methanol, and 17 g (0.16 mol) of chloromethyl thiocyanate were added dropwise at -5°. After slowly warming the reaction mixture to room temperature, it was subsequently stirred at 40° for a further 30 minutes and concentrated, the residue was extracted by shaking with water/ethylene chloride, the organic phase was concentrated and the oily residue was freed from chloromethyl thiocyanate residues by heating to 80°-100°/0.5 to 2 mm Hg for several hours; yield 30 g (this corresponds to a yield of 90% of the theretical conversion).

Workup

  1. concentrationconcentrated
  2. extractionthe residue was extracted
  3. stirringby shaking with water/ethylene chloride
  4. concentrationthe organic phase was concentrated
  5. temperatureby heating to 80°-100°/0.5 to 2 mm Hg for several hours

Sources & evidence

ORD record
ord-9ed003850a4c42b0b8a123db304b1824
Source dataset
uspto-grants-1980_04
Patent number
US04198428

Reaction notes

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