Potassium thiocyanate → HCID 21440137, compound

HRID 328957Notes

Reaction equation

HRID 328957 reaction equation
[S-:1][C:2]#[N:3].[K+].F[B-](F)(F)F.[C:10]([C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:21]([C:27]([OH:29])=[O:28])=[CH:20][C:19]=1[N+]#N)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>[Cu](SC#N)SC#N.O>[C:10]([C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:21]([C:27]([OH:29])=[O:28])=[CH:20][C:19]=1[S:1][C:2]#[N:3])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 516872Potassium thiocyanateHCID 21440168HCID 21440168, compound

Product 1

HCID 21440137HCID 21440137, compound

Reagents, catalysts & solvents 2

HCID 178514151HCID 178514151, compoundCatalystHCID 962WaterSolvent

Procedure

To a mixture of potassium thiocyanate (42 g), copper thiocyanate (4s g) and water (400 ml), 2-benzoyl-5-carboxy3-nitrobenzenediazonium tetrafluoroborate (prepared as described in Example 17, step A; 28 g) is added in portions while stirring at 45°-50° C. After the addition is completed, the mixture is stirred at about 50° C. for a further 4 hours and thereafter at room temperature for about 20 hours. The resulting precipitate is collected by filtration, washed with water and dried. The dried solids are then extracted with boiling ethanol (three portions of 250 ml, 100 ml, and 100 ml, respectively) and filtered hot. The combined filtrates are evaporated in vacuo and the residue is crystallized by trituration with 50% aqueous ethanol (100 ml). The material is collected by filtration, washed with cold 50% ethanol and dried. After recrystallization from aqueous ethanol, 4-benzoyl-5-nitro-3-thiocyanobenzoic acid is obtained with a melting point of 183.5°-184.5° C.

Workup

  1. additionis added in portions
  2. additionAfter the addition
  3. stirringthe mixture is stirred at about 50° C. for a further 4 hours
  4. filtrationThe resulting precipitate is collected by filtration
  5. washwashed with water
  6. customdried
  7. extractionThe dried solids are then extracted with boiling ethanol (three portions of 250 ml, 100 ml, and 100 ml
  8. filtrationrespectively) and filtered hot
  9. customThe combined filtrates are evaporated in vacuo
  10. customthe residue is crystallized by trituration with 50% aqueous ethanol (100 ml)
  11. filtrationThe material is collected by filtration
  12. washwashed with cold 50% ethanol
  13. customdried
  14. customAfter recrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-8d21980089be47379960e7026299acf7
Source dataset
uspto-grants-1977_04
Patent number
US04018794

Reaction notes

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