Dimethylformamide → 1,1-Dioxido-2-(4-bromobutyl)-1,2-benzisothiazol-3(2H)-one

HRID 962728Notes

Reaction equation

HRID 962728 reaction equation
[S:1]1([C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5](=[O:6])[NH:4]1)(=[O:3])=[O:2].[Na].[Br:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.CN(C)C=O>CCOCC.O>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][N:4]1[C:5](=[O:6])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[S:1]1(=[O:2])=[O:3]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 80561,4-DibromobutaneHCID 24181110Benzosulfinide sodium; Garantose sodium

Product 1

HCID 107817741,1-Dioxido-2-(4-bromobutyl)-1,2-benzisothiazol-3(2H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

The general procedure of J. D. Commerford and H. B. Donahue J. Org. Chem. 1956, 21, 583-4 was modified: A mixture of 6 g of sodium saccharin, 100 mL of 1,4-dibromobutane, and 5 mL of N,N-dimethylformamide was heated at 50° C. overnight. After cooling to ambient temperature, the mixture was diluted with 250 mL of ether and 50 mL of water. The aqueous layer was extracted with two additional 50 mL portions of ether and the combined organic extracts were dried over MgSO4 and concentrated under reduced pressure. The excess 1,4-dibromobutane was removed by short path vacuum distillation and the oily residue purified by crystallization from ether-hexane, mp 71°-2° C.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionThe aqueous layer was extracted with two additional 50 mL portions of ether
  3. dry with materialthe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe excess 1,4-dibromobutane was removed by short path vacuum distillation
  6. customthe oily residue purified by crystallization from ether-hexane, mp 71°-2° C.

Sources & evidence

ORD record
ord-622f8fc4833240958a72bb836dff86b4
Source dataset
uspto-grants-1998_06
Patent number
US05760054

Reaction notes

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