Thiophosgene → 3-Phenoxyphenylisothiocyanate

HRID 2070330Notes

Reaction equation

HRID 2070330 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15](Cl)(Cl)=[S:16].CCCCCC.CCOC(C)=O>CC(C)=O>[O:1]([C:8]1[CH:9]=[C:10]([N:11]=[C:15]=[S:16])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 771353-PhenoxyanilineHCID 21226206Ethyl acetate hexane

Product 1

HCID 220412813-Phenoxyphenylisothiocyanate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirring solution of 3-phenoxyaniline (185 mg, 1.0 mmol) in acetone (4.0 mL) at 0° C. was added thiophosgene (0.23 mL, 3.0 mmol) and the resulting reaction maintained for 30 min. The reaction determined complete by TLC (4:1 hexane/EtOAc). The reaction was concentrated, azeotroped with toluene and taken on without further purification.

Workup

  1. customthe resulting reaction
  2. temperaturemaintained for 30 min
  3. concentrationThe reaction was concentrated
  4. customazeotroped with toluene
  5. customtaken on without further purification

Sources & evidence

ORD record
ord-4e009959246f46d9aac7d6cec18cafe7
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

Loading…