Toluene → 5-tert.Butylcarbamylphthalid

HRID 1976862Notes

Reaction equation

HRID 1976862 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:9](=[O:10])[O:8][CH2:7]2)([OH:3])=O.CN(C=O)C.C1(C)C=CC=CC=1.[C:26]([NH2:30])([CH3:29])([CH3:28])[CH3:27]>S(Cl)(Cl)=O.C1COCC1>[C:26]([NH:30][C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:9](=[O:10])[O:8][CH2:7]2)=[O:3])([CH3:29])([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 6385Tert-ButylamineHCID 785171,3-Dihydro-1-oxoisobenzofuran-5-carboxylic acid

Product 1

HCID 111489925-tert.Butylcarbamylphthalid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24386Thionyl ChlorideSolvent

Procedure

5-Carboxyphthalid (36 g, 0.2 mole) is suspended in thionylchloride (100 mL). DMF (1.5 mL) is added and the mixture is refluxed for 1 hour. Toluene (200 mL) is added and the solvents are evaporated in vacuo. The residue is dissolved in THF (200 mL) and added to a solution of tert.butylamine (31 g, 0.42 mole) in THF (200 mL) at 5° C. The mixture is allowed to warm to room temperature and stirred overnight. The reaction is then poured into ice water (400 mL) and the precipitated crystals are filtered off. The crystals are washed with water (100 mL). Yield: 41 g, 87%. DSC onset: 189.5° C.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. customthe solvents are evaporated in vacuo
  3. dissolutionThe residue is dissolved in THF (200 mL)
  4. filtrationthe precipitated crystals are filtered off
  5. washThe crystals are washed with water (100 mL)
  6. custom189.5° C.

Sources & evidence

ORD record
ord-94938be2fcd0455e9ea8ccdb7d16aa64
Source dataset
uspto-grants-2001_05
Patent number
US06229026B1

Reaction notes

Loading…