1,3-Dichloro-2-isocyanatobenzene → HCID 44412843, compound

HRID 1038692Notes

Reaction equation

HRID 1038692 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[N:6]=[CH:5][N:4]=1.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=1[N:30]=[C:31]=[O:32]>O1CCOCC1>[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=1[NH:30][C:31](=[O:32])[N:2]([CH3:1])[C:3]1[CH:8]=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)=[CH:12][CH:11]=2)[N:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 6045371,3-Dichloro-2-isocyanatobenzeneHCID 57710358HCID 57710358, compound

Product 1

HCID 44412843HCID 44412843, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-methyl-N′-(4-morpholin-4-yl-phenyl)-pyrimidine-4,6-diamine (428.0 mg, 1.5 mmol), 2,6-dichlorophenyl isocyanate (310.2 mg, 1.65 mmol) in dry dioxane (5 mL) is shaken for 1.5 h at 80° C. After evaporation of the solvent in vacuo, the residue is purified by flash chromatography (CH2Cl2/CH3OH). 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 evaporation of the solvent in vacuo
  2. customthe residue is purified by flash chromatography (CH2Cl2/CH3OH)
  3. customThe combined pure fractions are evaporated
  4. customthe residue triturated with CH2Cl2
  5. filtrationthe solid filtered off
  6. customdried in vacuo

Sources & evidence

ORD record
ord-9f9ef365f8dc4027942b2753d5cecb97
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

Loading…