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

HRID 2306116Notes

Reaction equation

HRID 2306116 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)(O)=O.S(N)([NH2:17])(=O)=O.S(Cl)(Cl)=O.O>S1(CCCC1)(=O)=O>[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)#[N:17]

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 785171,3-Dihydro-1-oxoisobenzofuran-5-carboxylic acidHCID 82267Sulfamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
135 °C

Procedure

5-Carboxyphthalid (50 g, 0.28 mole) and sulfamide (31 g, 0.32 mole) were suspended in sulfolane (150 mL). Thionylchloride (41 g, 0.34 mole) was added and the temperature was raised to 130-140° C. for 2 hours. At about 90° C., gas evolution took place. The mixture was allowed to cool to 90° C. and water (150 mL) was added. The temperature was held at 85-90° C. for 15 min and then the solution was cooled to 35° C. The crystals were filtered off and washed with water (250 mL). The title compound was crystallised from acetic acid.Yield: 34.5 g, 77%. DSC onset: 203° C. Purity: 98.5% (hplc, peak area). 1H NMR (DMSO-d6, 500 MHz): 5.48 (2H, s), 8.03 (2H, s), 8.22 (1H, s). 13C NMR (DMSO-d6, 125 MHz): 70.0, 116.1, 188.0, 126.0, 127.5, 129.0, 132.8, 147.7, 169.3.

Workup

  1. customAt about 90° C.
  2. temperatureto cool to 90° C.
  3. temperaturethe solution was cooled to 35° C
  4. filtrationThe crystals were filtered off
  5. washwashed with water (250 mL)
  6. customThe title compound was crystallised from acetic acid
  7. custom203° C

Sources & evidence

ORD record
ord-ef4b8bf8fa524ff1a561fbcdf0232006
Source dataset
uspto-grants-2002_08
Patent number
US06441201B1

Reaction notes

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