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

HRID 514829Notes

Reaction equation

HRID 514829 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-522fe75e085945588571e3fc32547aab
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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