1,3-Dichloro-2-isocyanatobenzene → HCID 57710397, compound

HRID 1038685Notes

Reaction equation

HRID 1038685 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:6]=[CH:5][N:4]=1.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=1[N:28]=[C:29]=[O:30]>O1CCOCC1>[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=1[NH:28][C:29](=[O:30])[N:2]([CH3:1])[C:3]1[CH:8]=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:17])[F:18])[CH:11]=2)[N:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 6045371,3-Dichloro-2-isocyanatobenzeneHCID 66669958N4-Methyl-N6-[3-(trifluoromethyl)phenyl]-4,6-pyrimidinediamine

Product 1

HCID 57710397HCID 57710397, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-methyl-N′-(3-trifluoromethyl-phenyl)-pyrimidine-4,6-diamine (536.5 mg, 2 mmol), 2,6-dichlorophenyl isocyanate (413.6 mg, 2.2 mmol) in dry dioxane (5 mL) is shaken for 1 h at 80° C. After evaporation of the solvent in vacuo, the residue is distributed between ethyl acetate and half-saturated K2CO3 solution. The organic layer is dried over Na2SO4, evaporated, and the residue recrystallized from CH2Cl2/CH3OH. The solid residue is dried in vacuo to afford the title compound.

Workup

  1. customAfter evaporation of the solvent in vacuo
  2. dry with materialThe organic layer is dried over Na2SO4
  3. customevaporated
  4. customthe residue recrystallized from CH2Cl2/CH3OH
  5. customThe solid residue is dried in vacuo

Sources & evidence

ORD record
ord-63f03f155f2f41fb859de9a7deb2b119
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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