Carbon Tetrachloride → 2-{2'-[(Morpholinomethyleneamino)sulfonyl]-benzoyl}-1,2-benzoisothiazolin-3-one-1,1-dioxide

HRID 127639Notes

Reaction equation

HRID 127639 reaction equation
[CH:1]([N:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)=O.[S:9]1([C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:13](=[O:14])[NH:12]1)(=[O:11])=[O:10].[Na].C(Cl)(Cl)(Cl)Cl.[C:27](Cl)(Cl)=[O:28]>ClCCl>[O:6]1[CH2:7][CH2:8][N:3]([CH:1]=[N:12][S:9]([C:20]2[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=2[C:27]([N:12]2[C:13](=[O:14])[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[S:9]2(=[O:10])=[O:11])=[O:28])(=[O:11])=[O:10])[CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6371PhosgeneHCID 20417N-FormylmorpholineHCID 24181110Benzosulfinide sodium; Garantose sodium

Product 1

HCID 867375992-{2'-[(Morpholinomethyleneamino)sulfonyl]-benzoyl}-1,2-benzoisothiazolin-3-one-1,1-dioxideYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

N-formylmorpholine (3 ml) and 2.05 g of anhydrous sodium saccharin were added to 10 ml of dichloromethane. The mixture was cooled to -30° C., and with stirring, 1.65 ml (corresponding to about 5 millimoles of phosgene) of a carbon tetrachloride solution containing 30% of phosgene (W/V %) was added. The temperature of the mixture was raised to room temperature over a period of about 1 hour and stirred at room temperature for 2 hours. The solvent was distilled off under reduced pressure. Water was added to the remaining oily product, and under ice cooling, the mixture was stirred until the oily product crystallized. The crystals were collected by filtration, thoroughly washed with water, and dried to afford 1.70 g of white crystals (yield 73.4%), decomposition point:160°-169° C. Recrystallization of the crude crystals from acetone yielded white needle-like crystals having a decomposition point of 173° to 175° C.

Workup

  1. additionwas added
  2. temperatureThe temperature of the mixture was raised to room temperature over a period of about 1 hour
  3. stirringstirred at room temperature for 2 hours
  4. distillationThe solvent was distilled off under reduced pressure
  5. additionWater was added to the remaining oily product
  6. stirringunder ice cooling, the mixture was stirred until the oily product
  7. customcrystallized
  8. filtrationThe crystals were collected by filtration
  9. washthoroughly washed with water
  10. customdried

Sources & evidence

ORD record
ord-76907ab5b41a4fe0b73925e7ce9bf962
Source dataset
uspto-grants-1981_03
Patent number
US04256744

Reaction notes

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