Pyridine → HCID 83382924, compound

HRID 230555Notes

Reaction equation

HRID 230555 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:10])[CH3:9])=[CH:4][C:3]=1[NH2:11].N1C=CC=CC=1.Cl[C:19](Cl)([O:21]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[CH3:10][N:8]([CH3:9])[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([N:11]=[C:19]=[O:21])[CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 39235406HCID 39235406, compound

Product 1

HCID 83382924HCID 83382924, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

1.09 g (7.1 mmol) of 4-fluoro-N1,N1-dimethylbenzene-1,3-diamine followed by 4.6 cm3 of pyridine are added, at a temperature in the region of 5° C., under an argon atmosphere, to 2.82 g (9.5 mmol) of triphosgene in solution in 150 cm3 of dichloromethane. After stirring for 18 hours at a temperature in the region of 20° C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa), to give a residue which is triturated in 40 cm3 of tetrahydrofuran. After filtration, a solution of 5-dimethylamino-2-fluorophenyl isocyanate in approximately 0.14 N tetrahydrofuran is obtained, which solution is used directly in the subsequent step.

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. customto give a residue which
  3. customis triturated in 40 cm3 of tetrahydrofuran
  4. filtrationAfter filtration

Sources & evidence

ORD record
ord-ebf4f01a7e7a4e6ba4b2016398b927a3
Source dataset
uspto-grants-2009_07
Patent number
US07566736B2

Reaction notes

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