Potassium thiocyanate → HCID 42637795, compound

HRID 1816171Notes

Reaction equation

HRID 1816171 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[S-:19][C:20]#[N:21].[K+]>Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[CH:17][CH:18]=2)[C:20]([NH2:21])=[S:19])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 516872Potassium thiocyanate2×HCID 22496413HCID 22496413, compound

Product 1

HCID 42637795HCID 42637795, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

A mixture of 4-[(4-chlorophenylamino)methyl]benzoic acid (33.3 g, 127 mmol) and potassium thiocyanate (37 g, 382 mmol) in 1 N hydrochloric acid (500 mL) was refluxed for 16 hours. The suspension was filtered and washed with water. The solid was mixed with potassium thiocyanate (37 g, 382 mmol) and 1 N hydrochloric acid (500 mL) and the mixture was again refluxed for 16 hours. Filtration, washing with water and re-submission to the reaction conditions above afforded 30.2 g (70%) of 4-[1-(4-chlorophenyl)thioureidomethyl]benzoic acid as a solid.

Workup

  1. temperaturewas refluxed for 16 hours
  2. filtrationThe suspension was filtered
  3. washwashed with water
  4. temperaturethe mixture was again refluxed for 16 hours
  5. filtrationFiltration
  6. washwashing with water
  7. customre-submission to the reaction conditions

Sources & evidence

ORD record
ord-11b88bba6016439bb732b4ed2a6857d1
Source dataset
uspto-grants-2005_04
Patent number
US06881746B2

Reaction notes

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