2-Nitroaniline → 2-Nitrophenyl isothiocyanate

HRID 1736399Notes

Reaction equation

HRID 1736399 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[C:11](Cl)(Cl)=[S:12]>C1C=CC=CC=1>[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[N:6]=[C:11]=[S:12])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 69462-NitroanilineHCID 10040Thiophosgene

Product 1

HCID 1376902-Nitrophenyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 200 ml of benzene were added 22 g of 2-nitroaniline and 6.6 ml of thiophosgene. The mixture was refluxed for 2 hours. After cooling, the resulting crystals were removed by filtration and the filtrate was concentrated. The resulting residue was purified by a silica gel column chromatography (eluant: ethyl acetate/n-hexane=0/1→1/10) to obtain 8.0 g of 2-nitrophenyl isothiocyanate.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. customthe resulting crystals were removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customThe resulting residue was purified by a silica gel column chromatography (eluant: ethyl acetate/n-hexane=0/1→1/10)

Sources & evidence

ORD record
ord-f295848ab2d6420e9b148d366ef1526c
Source dataset
uspto-grants-1996_07
Patent number
US05541198

Reaction notes

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