Trimethylsilyl isocyanate → HCID 16795357, compound

HRID 709428Notes

Reaction equation

HRID 709428 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:9])[CH:8]=1)[NH2:5].C[Si]([N:14]=[C:15]=[O:16])(C)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:15]([NH2:14])=[O:16])[CH:6]=[C:7]([F:9])[CH:8]=1

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 965953,5-Difluoroaniline

Product 1

HCID 16795357HCID 16795357, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3,5-difluoroaniline (4.0 g, 31 mmol, 1.00 equiv) in CH2Cl2 (50 mL) under argon at room temperature was added dropwise trimethylsilyl isocyanate (3.56 g, 30.90 mmol, 1.00 equiv). The reaction mixture was stirred overnight and quenched by the dropwise addition of CH3OH (50 mL). The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by flash chromatography (silica gel, eluting with CHCl3/CH3OH (10:1 to 7:1)) to yield 2.0 g (38%) of the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6): δ ppm 8.96 (s, 1H), 7.16-7.10 (m, 2H), 6.72-6.66 (m, 1H), 6.07 (br s, 2H).

Workup

  1. customquenched by the dropwise addition of CH3OH (50 mL)
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by flash chromatography (silica gel, eluting with CHCl3/CH3OH (10:1 to 7:1))

Sources & evidence

ORD record
ord-3fc1d52816934f37840cd81ad66cf7d1
Source dataset
uspto-grants-2015_11
Patent number
US09181200B2

Reaction notes

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