Water → HCID 14723178, compound
Reaction equation
C(S[N:5]1[CH2:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[S:6]1(=[O:15])=[O:14])CC.[OH2:16].ClCl>C(O)(=O)C>[CH2:9]([N:5]1[CH2:9][C:8]2[CH:10]=[CH:11][CH:12]=[C:13]([S:6]([NH2:5])(=[O:14])=[O:16])[C:7]=2[S:6]1(=[O:14])=[O:15])[CH2:8][CH2:7][CH2:13][CH3:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of 9.5 g of 2-pentyl-7-(propylthio-2,3-dihydro-1,2-benzisothiazole-1,1-dioxide in 40 ml of acetic acid containing 1.3 ml of water was contacted with 7.0 ml of liquified chlorine at 10° to 15° C. and allowed to warm to 25° C. The excess chlorine was removed via a stream of nitrogen gas and the solution was poured onto ice. The resulting solid was filtered, washed with water and hexane, dried, dissolved in CH2Cl2 and contacted with 2.0 ml of liquified ammonia at -78° C. to 25° C. The mixture was added to 100 ml of 1N HCl and extracted with CH2Cl2. The extract was washed with water and brine, dried over MgSO4, concentrated and slurried in ether to give 6.35 g of the title compound as a white powder, m.p. 156°-160° C.
Workup
- customThe excess chlorine was removed via a stream of nitrogen gas
- additionthe solution was poured onto ice
- filtrationThe resulting solid was filtered
- washwashed with water and hexane
- customdried
- dissolutiondissolved in CH2Cl2
- customcontacted with 2.0 ml of liquified ammonia at -78° C. to 25° C
- additionThe mixture was added to 100 ml of 1N HCl
- extractionextracted with CH2Cl2
- washThe extract was washed with water and brine
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-33d8b9be27b64d2ca24883d3201df05f
- Source dataset
- uspto-grants-1989_06
- Patent number
- US04842639
Reaction notes
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