Triethylamine → HCID 69318710, compound

HRID 1619743Notes

Reaction equation

HRID 1619743 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH2:10][C:9]2([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[O:8][N:7]=1.C(N(CC)CC)C.[C:23]([C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24]>C1(C)C=CC=CC=1>[C:23]([C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34]([N:13]2[CH2:14][CH2:15][C:9]3([O:8][N:7]=[C:6]([C:2]4[S:1][CH:5]=[CH:4][N:3]=4)[CH2:10]3)[CH2:11][CH2:12]2)=[O:35])=[CH:29][CH:28]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27356951-Tert-butyl-4-isocyanatobenzeneHCID 59830356HCID 59830356, compound

Product 1

HCID 69318710HCID 69318710, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound O (0.150 g, 0.578 mmol) was dissolved in toluene (15 ml) and mixed successively with triethylamine (0.12 ml, 0.867 mmol) and 4-tert-butylphenyl isocyanate (0.102 ml, 0.578 mmol). The reaction mixture was heated to boiling point and boiled under reflux for 3 h. After cooling 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:EtOAc 1:1), the desired product was obtained in a yield of 52% (0.120 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:EtOAc 1:1)

Sources & evidence

ORD record
ord-565d7f300beb4c2b831df9d1582b9f70
Source dataset
uspto-grants-2014_07
Patent number
US08772307B2

Reaction notes

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