4-Chloro-2-nitroaniline → 4-Chloro-2-nitro-5-thiocyanatoaniline

HRID 619755Notes

Reaction equation

HRID 619755 reaction equation
BrBr.[Cl:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.[S-:14][C:15]#[N:16].[NH4+].[OH-].[Na+]>CO>[Cl:3][C:4]1[C:10]([S:14][C:15]#[N:16])=[CH:9][C:7]([NH2:8])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1

Participants

6

Reactant 4

HCID 69794-Chloro-2-nitroanilineHCID 14798Sodium HydroxideHCID 15666Ammonium thiocyanateHCID 24408Bromine

Product 1

HCID 218469914-Chloro-2-nitro-5-thiocyanatoanilineYield 89.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution 8 ml of bromine 7.00 g in methanol was added dropwise to a suspension 8 ml of 4-chloro-2-nitroaniline 6.61 g (38.3 mmol) and ammonium thiocyanate 7.00 g (92.0 mmol) in methanol, and the mixture was stirred for 2 hours at room temperature. The reaction mixture was poured into ice water and alkalized with 4N sodium hydroxide, and the precipitated crystals were filtered. The crystals were washed with water and with ether and dried under reduced pressure, and 4-chloro-2-nitro-5-thiocyanatoaniline 7.88 g (89.6%) was obtained.

Workup

  1. filtrationthe precipitated crystals were filtered
  2. washThe crystals were washed with water and with ether
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-fdc424fe95184d4185de012d040b3482
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

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