Water → HCID 22936684, compound

HRID 387993Notes

Reaction equation

HRID 387993 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][CH:15]=3)[CH:8]=2)=[CH:4][CH:3]=1.[C:24]1([N:30]=[C:31]=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[CH3:21][S:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:9]2[N:10]=[CH:11][N:12]=[C:7]([O:6][C:5]3[CH:22]=[CH:23][C:2]([NH:1][C:31]([NH:30][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:32])=[CH:3][CH:4]=3)[CH:8]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 3

HCID 962WaterHCID 7672Phenyl isocyanateHCID 22936907HCID 22936907, compound

Product 1

HCID 22936684HCID 22936684, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

N-(6-(4-Aminophenoxy)pyrimidin-4-yl)-4-methylsulfanylphenylamine (194 mg, 0.600 mmol) and phenyl isocyanate (78.6 mg, 0.660 mmol) were stirred in dimethylformamide (2 ml) at room temperature for 18 hours. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was suspended in ethyl acetate, the suspension was diluted with hexane, and the crystals were filtered out, washed with hexane and then blow-dried to obtain the title compound (250 mg, 0.564 mmol, 94%) as colorless crystals.

Workup

  1. washthe organic layer was washed with water and saturated saline
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe drying agent was filtered off
  4. distillationthe filtrate was distilled off under reduced pressure
  5. customThe obtained crude product
  6. filtrationthe crystals were filtered out
  7. washwashed with hexane
  8. customblow-dried

Sources & evidence

ORD record
ord-754795e0ccff403f88290d97f6f25126
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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