Potassium thiocyanate → HCID 19711336, compound

HRID 724916Notes

Reaction equation

HRID 724916 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.[S-:11][C:12]#[N:13].[K+]>Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:12](=[S:11])[NH2:13])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 516872Potassium thiocyanateHCID 34115665-Bromoindoline

Product 1

HCID 19711336HCID 19711336, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 5-bromoindoline (14.8 g, 75 mmol) in 200 mL of 1N aqueous hydrochloric acid was treated with potassium thiocyanate (34.0 g, 350 mmol) in portions. The mixture was heated at reflux for 1 h and was then cooled to room temperature. The precipitate was collected, washed with water, and recrystallized from 2-propanol to afford (in two crops) 14.1 g (73%) of 5-bromoindoline-1-thiocarboxamide as a light yellow, fluffy solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 h
  3. customThe precipitate was collected
  4. washwashed with water
  5. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-e887c3a8da6c404ebf29fa6a3686962f
Source dataset
uspto-grants-1998_01
Patent number
US05705515

Reaction notes

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