4-Chlorophenyl Isocyanate → HCID 131727719, compound

HRID 1432554Notes

Reaction equation

HRID 1432554 reaction equation
[CH:1]1([C:10]([OH:12])=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.[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]([C:1]2([C:10]([OH:12])=[O:11])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][NH:2]2)=[O:22])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 133813692,3-Dihydro-1H-isoindole-1-carboxylic acid

Product 1

HCID 131727719HCID 131727719, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (D,L) 2,3-dihydro-1H-isoindole-1-carboxylic acid (372 mg, 2.28 mmol) in 3N aq. NaOH (10 mL), a solution of 4-chlorophenylisocyanate (530 mg, 3.66 mmol) in dioxane (6 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 to give the titled compound as a solid (550 mg), which was sufficiently pure to be used in the next reaction. MS 317.0 and 319.0 (M+H, Cl pattern).

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

Sources & evidence

ORD record
ord-178b675a2cc843fab29e70e6da723b47
Source dataset
uspto-grants-2009_11
Patent number
US07612089B2

Reaction notes

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