4-Chloro-3-(trifluoromethyl)aniline → 1-Chloro-4-isothiocyanato-2-(trifluoromethyl)benzene

HRID 491581Notes

Reaction equation

HRID 491581 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:12])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:13](N1C=CN=C1)(N1C=CN=C1)=[S:14]>C(Cl)Cl>[Cl:12][C:5]1[CH:4]=[CH:3][C:2]([N:1]=[C:13]=[S:14])=[CH:7][C:6]=1[C:8]([F:9])([F:10])[F:11]

Participants

4

Reactant 2

HCID 675744-Chloro-3-(trifluoromethyl)anilineHCID 802641,1'-Thiocarbonyldiimidazole2×

Product 1

HCID 5200261-Chloro-4-isothiocyanato-2-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 5-amino-2-chlorobenzotrifluoride (0.932 g, 4.76 mmol) in 30 mL CH2Cl2 was added 1,1′-thiocarbonyldiimidazole (0.976 g, 1.15 mmol). The reaction was warmed to RT and stirred for 45 min. The reaction was stirred for an additional 1 h, during which additional 1,1′-thiocarbonyldiimidazole (0.50 g and 0.20 g) was added at 30 min intervals. The reaction was concentrated down to a small volume and purified by short column silica gel chromatography using EtOAc:hexanes (15:75), to obtain the title compound.

Workup

  1. additionwas added at 30 min intervals
  2. concentrationThe reaction was concentrated down to a small volume
  3. custompurified by short column silica gel chromatography

Sources & evidence

ORD record
ord-5f04d5bb23754de4b988eba51c949843
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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