Ethyl isocyanate → (E)-1-ethyl-3-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}urea

HRID 1821320Notes

Reaction equation

HRID 1821320 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])=[N:2]1.C(N(CC)CC)C.[CH2:26]([N:28]=[C:29]=[O:30])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[CH2:26]([NH:28][C:29]([NH:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1/[CH:11]=[CH:10]/[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][N:2]=1)=[O:30])[CH3:27]

Participants

7

Reactant 4

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 69001756HCID 69001756, compound

Product 1

HCID 69002967(E)-1-ethyl-3-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}ureaYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (E)-2-[2-(1H-indazol-3-yl)vinyl]phenylamine (60 mg, 0.26 mmol) in THF (1.5 mL) was added with triethylamine (11 μL, 0.08 mmol) and ethyl isocyanate (40.3 μL, 0.51 mmol), followed by stirring at room temperature for 5 hours. Further, the reaction mixture was added with potassium carbonate, stirred for 30 minutes and added with water. The precipitated solid was collected by filtration and the solid was triturated in ethanol to obtain Compound 21 (53 mg, 68%).

Workup

  1. stirringstirred for 30 minutes
  2. filtrationThe precipitated solid was collected by filtration
  3. customthe solid was triturated in ethanol

Sources & evidence

ORD record
ord-db3f3a646876447586c931da9ea339a5
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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