Thiophosgene → 3-Phenoxyphenylisothiocyanate

HRID 1915707Notes

Reaction equation

HRID 1915707 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-5db60a5e706848e79e22001091fd081d
Source dataset
uspto-grants-2013_12
Patent number
US08614330B2

Reaction notes

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