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

HRID 2306117Notes

Reaction equation

HRID 2306117 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
137.5 °C

Procedure

Wet 5-carboxyphthalid (14 kg, approx. 6.3 kg dry, 35 mole) was suspended in sulfolane (23.5 kg). The water was removed by azeotropic distillation with toluene. Sulfamide (3.9 kg, 41 mole) and thionyl chloride (5.8 kg, 48 mole were added and the temperature was raised to 135-140° C. for 5 hours. At about 90° C. gas evolution took place. The mixture was allowed to cool to 90° C. and water (21.3 kg) 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 (14.2 kg). The title compound was crystallised from acetic acid. Yield: 3.8 kg, 68%. Purity: 99.5% (hplc, peak area).

Workup

  1. customThe water was removed by azeotropic distillation with toluene
  2. customAt about 90° C.
  3. temperatureto cool to 90° C.
  4. temperaturethe solution was cooled to 35° C
  5. filtrationThe crystals were filtered off
  6. washwashed with water (14.2 kg)
  7. customThe title compound was crystallised from acetic acid

Sources & evidence

ORD record
ord-5dd9151b96614f8db370de4b4e21193c
Source dataset
uspto-grants-2002_08
Patent number
US06441201B1

Reaction notes

Loading…