Toluene → 1,3-Dihydro-1-oxoisobenzofuran-5-carbonitrile

HRID 1072766Notes

Reaction equation

HRID 1072766 reaction equation
CC1(C)CO[C:4]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[C:12](=[O:16])[O:11][CH2:10]3)=[N:3]1.CN(C)C=O.C1(C)C=CC=CC=1>S(Cl)(Cl)=O>[C:4]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[O:11][CH2:10]2)#[N:3]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6228DimethylformamideHCID 113221954,4-Dimethyl-2-(1-oxo-1,3-dihydroisobenzofuran-5-yl)oxazoline

Product 1

HCID 8212181,3-Dihydro-1-oxoisobenzofuran-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

To a suspension of 4,4-dimethyl-2-(1-oxo-1,3-dihydroisobenzofuran-5-yl)oxazoline (23.1 g, 0.1 mol) in thionyl chloride (36 mL) is slowly added N,N-dimethylformamide (5 ml). The solution is heated at reflux for 1 hour and then allowed to cool to room temperature over 3 hours. Then toluene (150 mL) is added and the suspension is filtered and washed with toluene (2×50 mL). The wet crystals are taken into deionized water (150 mL) and the pH is adjusted to 8.0 with 25% aqueous ammonia. The solid is filtered and washed with deionized water (2×50 mL) and dried at 60° C. under reduced pressure. Yield: 11.9 g (75%) of an off-white product having a purity (HPLC, peak area)=92%. An analytical pure sample is obtained by crystallisation from acetic acid or toluene. 1H NMR (DMSO d-6, 500 MHz): 5.48 (2H, s), 8.04 (2H, s+s), 8.22 (1H, s).

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux for 1 hour
  3. filtrationthe suspension is filtered
  4. washwashed with toluene (2×50 mL)
  5. filtrationThe solid is filtered
  6. washwashed with deionized water (2×50 mL)
  7. customdried at 60° C. under reduced pressure
  8. customAn analytical pure sample is obtained by crystallisation from acetic acid or toluene

Sources & evidence

ORD record
ord-49afc79d1f0b47d0bbc66eddce2050cb
Source dataset
uspto-grants-2005_06
Patent number
US06911548B2

Reaction notes

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