1-Isocyanato-2-phenylbenzene → biphenyl-2-yl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester

HRID 2120248Notes

Reaction equation

HRID 2120248 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]([N:7]=[C:8]=[O:9])=[CH:3][CH:4]=[CH:5][CH:6]=1.[OH:16][CH2:17][CH2:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:20]=1[CH2:21][C:22](=[O:28])[NH:23]2>O1CCCC1.CN(C)C=O.N1C=CC=CC=1>[O:28]=[C:22]1[CH2:21][C:20]2[C:24](=[CH:25][CH:26]=[CH:27][C:19]=2[CH2:18][CH2:17][O:16][C:8](=[O:9])[NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:23]1

Participants

6

Reactant 2

HCID 2222801-Isocyanato-2-phenylbenzeneHCID 109430044-(2-Hydroxyethyl)indolin-2-one

Product 1

HCID 9820821biphenyl-2-yl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl esterYield 80%

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

2-Biphenylyl isocyanate (1.15 mL, 6.7 mmol) was added dropwise to a stirred mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (709 mg, 4 mmol) in tetrahydrofuran (8 mL), dimethylforamide (2 mL) and pyridine (3 drops) under nitrogen atmosphere. The mixture was heated at 80° C. for 15 hours. The reaction was cooled, quenched with 1 N sodium hydroxide solution (100 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on silica gel eluting with ethyl acetate:hexane 3:2 to give 1.188 g (80%) of biphenyl-2-yl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester as a white fluffy solid.

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with 1 N sodium hydroxide solution (100 mL)
  3. extractionextracted with ethyl acetate (200 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting with ethyl acetate:hexane 3:2

Sources & evidence

ORD record
ord-4f1a74cccfe84908b89f389314c213f9
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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