Triethylamine → HCID 69319114, compound

HRID 1619742Notes

Reaction equation

HRID 1619742 reaction equation
[Cl:1][C:2]1[C:3]([C:8]2[CH2:12][C:11]3([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[O:10][N:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:25]([C:29]1[CH:34]=[CH:33][C:32]([N:35]=[C:36]=[O:37])=[CH:31][CH:30]=1)([CH3:28])([CH3:27])[CH3:26]>C1(C)C=CC=CC=1>[C:25]([C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36]([N:15]2[CH2:16][CH2:17][C:11]3([O:10][N:9]=[C:8]([C:3]4[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=4)[CH2:12]3)[CH2:13][CH2:14]2)=[O:37])=[CH:31][CH:30]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27356951-Tert-butyl-4-isocyanatobenzeneHCID 59830355HCID 59830355, compound

Product 1

HCID 69319114HCID 69319114, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound K (0.130 g, 0.451 mmol) was dissolved in toluene (15 ml) and triethylamine (0.12 ml, 0.867 mmol) and 4-tert-butylphenyl isocyanate (0.08 ml, 0.451 mmol) were successively added. The reaction mixture was heated to boiling point and boiled under reflux for 3 h. After cooling of the reaction mixture to RT, the mixture was stirred for 36 h. The reaction mixture was extracted with EtOAc (3×20 ml). The combined organic phases were washed with sat. Na2HCO3 solution (10 ml), dried over Na2SO4 and concentrated to dryness under vacuum. After purification of the residue by column chromatography (hexane:EtOAc1:1), the product was obtained in a yield of 83% (0.160 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 h
  3. extractionThe reaction mixture was extracted with EtOAc (3×20 ml)
  4. washThe combined organic phases were washed with sat. Na2HCO3 solution (10 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness under vacuum
  7. customAfter purification of the residue by column chromatography (hexane:EtOAc1:1)
  8. customthe product was obtained in a yield of 83% (0.160 g)

Sources & evidence

ORD record
ord-4d487d0fd61240c4980b03e3f1dc4fe9
Source dataset
uspto-grants-2014_07
Patent number
US08772307B2

Reaction notes

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