1-Tert-butyl-4-isocyanatobenzene → HCID 58659380, compound

HRID 1993513Notes

Reaction equation

HRID 1993513 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[CH:3]=1.[C:16]([C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[O:28])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH:13][C:27]([NH:26][C:23]3[CH:24]=[CH:25][C:20]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:21][CH:22]=3)=[O:28])=[CH:11][CH:10]=2)[CH:3]=1

Participants

5

Reactant 2

HCID 27356951-Tert-butyl-4-isocyanatobenzeneHCID 226137114-((6-Chloropyrimidin-4-yl)oxy)aniline

Product 1

HCID 58659380HCID 58659380, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(6-chloro-pyrimidin-4-yl-oxy)-aniline (Stage 21.1; 3.77 g, 15 mmol) in THF (55 ml) under N2-atmosphere, 4-tertbutylphenyl isocyanate (5.26 g, 30 mmol) dissolved in THF (5 ml) is added. During stirring for 1 h at rt a suspension is formed. The mixture is then re-dissolved in AcOEt and a solution of NaHCO3 in water, the aqueous layer separated off and extracted twice with AcOEt. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated in vacuo. Stirring of the resulting solid in Et2O finally yields the title compound: m.p.: 111-112° C.; 1H-NMR (DMSO-d6): 8.75 (s, HN), 8.65 (s, 1H), 8.62 (s, HN), 7.51 (d, 2H), 7.36 (d, 2H), 7.33 (s, 1H), 7.31 (d, 2H), 7.17 (d, 2H), 1.27 (Me3C).

Workup

  1. additionis added
  2. customis formed
  3. customa solution of NaHCO3 in water, the aqueous layer separated off
  4. extractionextracted twice with AcOEt
  5. washThe organic phases are washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. stirringStirring of the resulting solid in Et2O

Sources & evidence

ORD record
ord-9cdbd9285beb4c79b5e46ce2cc9aa2f8
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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