Ethanolamine → HCID 69659305, compound

HRID 1829063Notes

Reaction equation

HRID 1829063 reaction equation
[N:1]([CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:23])[O:6]1)=[C:2]=[O:3].[OH:24][CH2:25][CH2:26][NH2:27]>C1COCC1>[OH:24][CH2:25][CH2:26][NH:27][C:2]([NH:1][CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:23])[O:6]1)=[O:3]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 86590934HCID 86590934, compound

Product 1

HCID 69659305HCID 69659305, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3-(3-isocyanatomethyl-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (75 mg, 0.24 mmol) and 2-hydroxyethylamine (44.4 μl, 0.74 mmol) in THF (2.0 ml) was stirred at room temperature for 25 minutes and then heated at 60° C. for 5 minutes. The reaction was partitioned between EtOAc and water. The organic layer was washed with water, brine, dried with anhydrous Na2SO4, and rotary evaporated to result in a brown-yellow solid. The brown-yellow solid was chromatographed through silica gel column (CHCl3 to 5% MeOH/CHCl3 gradient) to give 1-(2-hydroxy-ethyl)-3-[3-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-ylmethyl]-urea as a yellow solid (18 mg, 20%).

Workup

  1. customThe reaction was partitioned between EtOAc and water
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried with anhydrous Na2SO4
  4. customrotary evaporated
  5. customto result in a brown-yellow solid
  6. customThe brown-yellow solid was chromatographed through silica gel column (CHCl3 to 5% MeOH/CHCl3 gradient)

Sources & evidence

ORD record
ord-7d4b8e002d7b4ad091b3841d4f7f8605
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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