Hydrochloric Acid → 3-Methylsulfonyl-4-trifluoromethoxyphenyl isocyanate

HRID 412451Notes

Reaction equation

HRID 412451 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][C:11]=1[O:12][C:13]([F:16])([F:15])[F:14])[NH2:8])(=[O:4])=[O:3].Cl.C1(C)C=CC=CC=1.[O:25]=[C:26](Cl)OC(Cl)(Cl)Cl>C(OCC)(=O)C>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([N:8]=[C:26]=[O:25])[CH:9]=[CH:10][C:11]=1[O:12][C:13]([F:14])([F:15])[F:16])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 10426Diphosgene2×HCID 223111603-Methylsulfonyl-4-trifluoromethoxyaniline

Product 1

HCID 223111583-Methylsulfonyl-4-trifluoromethoxyphenyl isocyanate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To 3-methylsulfonyl-4-trifluoromethoxyaniline (2.0 mmol, 500 mg) dissolved in ethyl acetate (6 mL) was added 3 N hydrochloric acid in ethyl acetate (5 mL) followed by concentration in vacuo. The residue was treated with toluene (3×5 mL) and each time concentrated in vacuo. To the residue was added toluene (10 mL) and diphosgene (6 mmol, 0.73 mL) under a nitrogen atmosphere and the suspension was gently refluxed for 2 hours. Additional diphosgene (6 mmol, 0.73 mL) was added and refluxing was continued overnight. The reaction mixture was concentrated in vacuo to afford 3-methylsulfonyl-4-trifluoromethoxyphenyl isocyanate.

Workup

  1. concentrationfollowed by concentration in vacuo
  2. additionThe residue was treated with toluene (3×5 mL)
  3. concentrationeach time concentrated in vacuo
  4. temperaturethe suspension was gently refluxed for 2 hours
  5. temperaturerefluxing
  6. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-7959a387029d4cbc906313c363a1ad58
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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