Potassium thiocyanate → HCID 20566324, compound

HRID 848118Notes

Reaction equation

HRID 848118 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:13][C:14]2[N:18]=[CH:17][O:16][N:15]=2)=[CH:8][CH:7]=1.[S-:19][C:20]#[N:21].[K+].C(=O)([O-])O.[Na+]>O.C(O)(=O)C.S(=O)(=O)(O)O>[S:19]([C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:13][C:14]2[N:18]=[CH:17][O:16][N:15]=2)=[CH:8][CH:7]=1)[C:20]#[N:21]

Participants

8

Reactant 4

HCID 516872Potassium thiocyanateHCID 516892Sodium BicarbonateHCID 20566329HCID 20566329, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20566324HCID 20566324, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

Sodium nitrite (1.38 g, 0.02 mol) in water (15 ml) was added dropwise to a solution of 3-(4-aminophenylthiomethyl)-1,2,4-oxadiazole, (4.14 g, 0.02 mol) in acetic acid (120 ml) and 2 N sulphuric acid (40 ml) at 0° with stirring. The pale yellow solution thus obtained was added over 30 min. to a stirred mixture of cuprous thiocyanate (6 g) and potassium thiocyanate (60 g) in water (100 ml) at 0°, and the mixture stirred overnight. The mixture was then neutralised with solid sodium hydrogen carbonate and extracted with chloroform to give a yellow solid which was recrystallised from propan-2-ol to give 3-(4-thiocyanatophenylthiomethyl)-1,2,4-oxadiazole, m.p. 78°.

Workup

  1. customThe pale yellow solution thus obtained
  2. stirringthe mixture stirred overnight
  3. extractionextracted with chloroform
  4. customto give a yellow solid which
  5. customwas recrystallised from propan-2-ol

Sources & evidence

ORD record
ord-d81b8ef0e5a64d9db041c87ddddc8ce3
Source dataset
uspto-grants-1981_10
Patent number
US04294842

Reaction notes

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