4-Chlorophenyl Isocyanate → HCID 69664943, compound

HRID 1432555Notes

Reaction equation

HRID 1432555 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10]([OH:12])=[O:11].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[CH:16][CH:15]=1>[OH-].[Na+].O1CCOCC1>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH:2]2[C:10]([OH:12])=[O:11])=[O:22])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 86074Indoline-2-carboxylic acid

Product 1

HCID 69664943HCID 69664943, compoundYield 30.5%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (D,L) indoline-2-carboxylic acid (548 mg, 3.36 mmol) in 1N aq. NaOH (8 mL), a solution of 4-chlorophenylisocyanate (728 mg, 4.74 mmol) in dioxane (8 mL) was added. The mixture was stirred at room temperature overnight. It was then washed with Et2O (2×). The aqueous layer was separated, acidified with 4N HCl to pH 1 to 2. The product was extracted with EtOAc. The EtOAc solution was dried over Na2SO4, concentrated in vacuo. The residue was purified by HPLC to give the desired product as a powder (325 mg).

Workup

  1. washIt was then washed with Et2O (2×)
  2. customThe aqueous layer was separated
  3. extractionThe product was extracted with EtOAc
  4. dry with materialThe EtOAc solution was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-da559fd132b949069534bbdeb0392b83
Source dataset
uspto-grants-2009_11
Patent number
US07612089B2

Reaction notes

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