2-Fluoro-6-nitroaniline → 2-Fluoro-6-nitrophenylthiocyanate

HRID 2202365Notes

Reaction equation

HRID 2202365 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:3]=1N.N([O-])=O.[Na+].[S-:16][C:17]#[N:18].[K+]>S(=O)(=O)(O)O.O>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:3]=1[S:16][C:17]#[N:18]

Participants

6

Reactant 3

HCID 873162-Fluoro-6-nitroanilineHCID 516872Potassium thiocyanateHCID 23668193Sodium Nitrite

Product 1

HCID 904190222-Fluoro-6-nitrophenylthiocyanateYield 99.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 2-fluoro-6-nitroaniline (3 g, 0.02 mol) in conc. sulphuric acid (30 mL) and water (30 mL) was diazotized at 0-3° C. for 90 min with aqueous sodium nitrite (1.45 g, 0.021 mol). After addition of potassium thiocyanate (2.522 g, 0.026 mol) in water (10 mL), the diazo-liquor was stirred vigorously into a suspension of cuprous thiocyanate (6.05 g, 0.05 mol) in water (20 mL) at 5° C. After stirring at 5° C. for 2 hr, the mixture was then heated at 70° C. for 20 min, then was cooled overnight, filtered, and the cake extracted with EtOAc to get the crude product (3.96 g) which was used in the next step without further purification. LC-MS: m/z 199.2 (M+H)+

Workup

  1. temperaturethe mixture was then heated at 70° C. for 20 min
  2. temperaturewas cooled overnight
  3. filtrationfiltered
  4. extractionthe cake extracted with EtOAc

Sources & evidence

ORD record
ord-9dbdd951599947b4989f18d7a491929f
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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