Phenyl isocyanate → HCID 67297600, compound

HRID 629018Notes

Reaction equation

HRID 629018 reaction equation
[CH3:1][S:2][C:3]1[C:4]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[N:7][CH:8]=1.[C:22]1([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C.C1COCC1>[CH3:1][S:2][C:3]1[C:4]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:29]([NH:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:30])=[CH:11][CH:10]=2)=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 67295403HCID 67295403, compound

Product 1

HCID 67297600HCID 67297600, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(5-(methylthio)-4-morpholinopyrimidin-2-yl)benzeneamine (0.1 g, 0.33 mmole), co-solvent (5 ml, DMF/THF=6/40) and phenyl isocyanate (0.2 ml, 0.92 mmole) was heated to 80° C. After 12 hrs, the reaction mixture was cooled, and the THF removed in vacuo. Then the mixture was diluted with EA, washed with brine, and dried (MgSO4). The solvent was removed in vacuo. Purification of the residue on silica gel (EA/Hex=1/2) yielded the desired compound (42.2 mg, 30.4%).

Workup

  1. temperaturethe reaction mixture was cooled
  2. customthe THF removed in vacuo
  3. additionThen the mixture was diluted with EA
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customPurification of the residue on silica gel (EA/Hex=1/2)

Sources & evidence

ORD record
ord-cdbdc5a0a9c74437a56a44475a3b42ae
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

Loading…