Pseudosaccharin chloride → HCID 178479775, compound

HRID 1154722Notes

Reaction equation

HRID 1154722 reaction equation
[Cl:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4](=[O:12])(=[O:11])[N:3]=1.[N:13]1([CH2:19][C:20]2[CH:21]=[C:22]([CH:28]=[CH:29][CH:30]=2)[O:23][CH2:24][CH2:25][CH2:26][NH2:27])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>C(Cl)(Cl)Cl>[ClH:1].[N:13]1([CH2:19][C:20]2[CH:21]=[C:22]([CH:28]=[CH:29][CH:30]=2)[O:23][CH2:24][CH2:25][CH2:26][NH:27][C:2]2[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[S:4](=[O:12])(=[O:11])[N:3]=2)[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 64783Pseudosaccharin chlorideHCID 133908193-[3-(4-Morpholinylmethyl)phenoxy]1-propanamine

Product 1

HCID 178479775HCID 178479775, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1.37 g (0.0068 moles) of 3-chlorobenzoisothiazole 1,1-dioxide is added dropwise to 1.7 g (0.0068 moles) of 3-[3-(4-morpholinylmethyl)phenoxy]-1-propanamine in 150 ml of gently refluxing chloroform, over 30 minutes. The reflux is continued for 15 minutes after the end of the addition, then the reaction mixture is evaporated to dryness. The residue is treated with ethanol-ethyl acetate, causing the formation of a yellow-white solid. m.p. 21° C. (dec.) Recrystallization of the crude product from ethanol gave a m.p. of 215° C. (dec.) (1.7 g yield).

Workup

  1. additionafter the end of the addition
  2. customthe reaction mixture is evaporated to dryness
  3. additionThe residue is treated with ethanol-ethyl acetate
  4. customm.p. 21° C. (dec.) Recrystallization of the crude product from ethanol
  5. customgave
  6. customa m.p. of 215° C. (dec.) (1.7 g yield)

Sources & evidence

ORD record
ord-e8af5cb18884464192cf3acc16af092e
Source dataset
uspto-grants-1984_12
Patent number
US04490527

Reaction notes

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