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

HRID 2306118Notes

Reaction equation

HRID 2306118 reaction equation
Cl[C:2]([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.S(N)([NH2:17])(=O)=O.O>S1(CCCC1)(=O)=O>[C:2]([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

5

Reactant 3

HCID 962WaterHCID 82267SulfamideHCID 98155555-Chlorocarbonylphthalide

Product 1

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

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
135 °C

Procedure

5-Chlorocarbonylphthalid (24.3 g, 0.124 mole) was dissolved in sulfolane (51 g). Sulfamide (13.8 g 0.144 mole) was added and the temperature was raised to 135° C. for 3 hours. At about 90° C., gas evolution took place. The mixture was allowed to cool and water (100 g) was added. The temperature was held at 85-90° C. for 5 min and then the solution was cooled to 60° C. The crystals were filtered off and washed with water (60 g) and acetic acid (30 g). Then the title compound was dried in vacuo. Yield: 19 g, 96%. Purity: 98.2% (hplc, peak area).

Workup

  1. customAt about 90° C.
  2. temperatureto cool
  3. temperaturethe solution was cooled to 60° C
  4. filtrationThe crystals were filtered off
  5. washwashed with water (60 g) and acetic acid (30 g)
  6. dry with materialThen the title compound was dried in vacuo

Sources & evidence

ORD record
ord-04675e1251234481afd79f63b5410811
Source dataset
uspto-grants-2002_08
Patent number
US06441201B1

Reaction notes

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