1,3-Dichloro-2-isocyanatobenzene → HCID 57710265, compound

HRID 1038697Notes

Reaction equation

HRID 1038697 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:15]=[C:14]([NH:16][CH3:17])[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=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]>CN(C)C=O>[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[NH:27][C:28](=[O:29])[N:16]([C:14]1[CH:15]=[C:10]([NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([N:2]([CH3:1])[CH3:18])[CH:4]=2)[N:11]=[CH:12][N:13]=1)[CH3:17]

Participants

4

Reactant 2

HCID 6045371,3-Dichloro-2-isocyanatobenzene2×HCID 66670065HCID 66670065, compound

Product 1

HCID 57710265HCID 57710265, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of N-(3-dimethylamino-phenyl)-N′-methyl-pyrimidine-4,6-diamine (243.3 mg, 1 mmol), 2,6-dichlorophenyl isocyanate (188 mg, 1 mmol) in dry dimethylformamide (2.5 mL) is shaken for 14 h at 90° C. Two additional portions (188 mg, 1 mmol each) of 2,6-dichlorophenyl isocyanate are added after 14 h and 26 h. After 38 h the reaction mixture is evaporated in vacuo and the residue is distributed between ethyl acetate and half-saturated K2CO3 solution. The organic layer is dried over Na2SO4, evaporated, and the residue purified by flash chromatography (hexane/ethyl acetate). The combined pure fractions are evaporated, the residue triturated with CH2Cl2 and the solid filtered off and dried in vacuo to afford the title compound.

Workup

  1. customAfter 38 h the reaction mixture is evaporated in vacuo
  2. dry with materialThe organic layer is dried over Na2SO4
  3. customevaporated
  4. customthe residue purified by flash chromatography (hexane/ethyl acetate)
  5. customThe combined pure fractions are evaporated
  6. customthe residue triturated with CH2Cl2
  7. filtrationthe solid filtered off
  8. customdried in vacuo

Sources & evidence

ORD record
ord-a051174cb3594565b1c1c74ff41a554b
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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