1,3-Dichloro-2-isocyanatobenzene → HCID 57710307, compound

HRID 1038679Notes

Reaction equation

HRID 1038679 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=2)[CH:4]=1.[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[N:27]=[C:28]=[O:29]>O1CCOCC1>[C:16]([C:13]1[CH:12]=[CH:11][C:10]([NH:9][C:5]2[N:6]=[CH:7][N:8]=[C:3]([N:2]([CH3:1])[C:28]([NH:27][C:21]3[C:20]([Cl:19])=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:26])=[O:29])[CH:4]=2)=[CH:15][CH:14]=1)(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 6045371,3-Dichloro-2-isocyanatobenzeneHCID 66669911HCID 66669911, compound

Product 1

HCID 57710307HCID 57710307, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-[4-(6-methylamino-pyrimidin-4-ylamino)-phenyl]-ethanone (3.77 g, 15.56 mmol), 2,6-dichlorophenyl isocyanate (3.22 g, 17.12 mmol) in dry dioxane (30 mL) is shaken for 16 h at 80° C. After evaporation of the solvent in vacuo, the residue is distributed between ethyl acetate and half-saturated K2CO3 solution. The precipitate is filtered off and washed with H2O and ethyl acetate. The solid residue is suspended in methanol, heated to reflux for several h and the hot yellow suspension filtered. This procedure is repeated once. The residue obtained after the second filtration is washed with CH3OH and dried in vacuo to afford the title compound.

Workup

  1. customAfter evaporation of the solvent in vacuo
  2. filtrationThe precipitate is filtered off
  3. washwashed with H2O and ethyl acetate
  4. temperatureheated
  5. temperatureto reflux for several h
  6. filtrationthe hot yellow suspension filtered
  7. customThe residue obtained
  8. filtrationafter the second filtration
  9. washis washed with CH3OH
  10. customdried in vacuo

Sources & evidence

ORD record
ord-ddd6e991f0af4473b590b999f1d6f034
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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