Trimethylsilyl isocyanate → HCID 16795357, compound

HRID 1496940Notes

Reaction equation

HRID 1496940 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 silica gel column chromatography using CHCl3/CH3OH (10:1 to 7:1) as eluent to yield the title compound (2.0 g, 38%) 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 silica gel column chromatography

Sources & evidence

ORD record
ord-ee25cfb4be374894bcbff684918429ab
Source dataset
uspto-grants-2015_12
Patent number
US09199945B2

Reaction notes

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