Acetonitrile → HCID 178479773, compound

HRID 1154718Notes

Reaction equation

HRID 1154718 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6](=O)[NH:7][S:8](=[O:10])(=[O:9])[C:4]=2[CH:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:15].[N:20]1([CH2:26][C:27]2[CH:28]=[C:29]([CH:35]=[CH:36][CH:37]=2)[O:30][CH2:31][CH2:32][CH2:33][NH2:34])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(#N)C>ClC1C=CC=CC=1Cl>[ClH:15].[N:20]1([CH2:26][C:27]2[CH:28]=[C:29]([CH:35]=[CH:36][CH:37]=2)[O:30][CH2:31][CH2:32][CH2:33][NH:34][C:6]2[C:5]3[CH:12]=[CH:13][C:2]([Br:1])=[CH:3][C:4]=3[S:8](=[O:10])(=[O:9])[N:7]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24819Phosphorus pentachlorideHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 105409966-Bromo-2,3-dihydro-1,2-benzothiazole-1,1,3-trione

Product 1

HCID 178479773HCID 178479773, compound

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A mixture of 4.00 g (15 mmol) 6-bromo-1,2-benzisothiazol-3(2H)-one 1,1-dioxide and 3.57 g (17 mmol) phosphorus pentachloride in 5 ml o-dichlorobenzene is heated from ambient temperature to 160° C. over one hour and is held at that temperature for one additional hour. Upon cooling, liquids are removed in vacuo and the residual 6-bromo-3-chlorobenzisothiazole 1,1-dioxide is suspended in acetonitrile and added portionwise to a solution of 3.7 g (15 mmol) 3-[3-[(1-piperidinyl)methyl]phenoxy]propylamine in refluxing acetonitrile. Heating at reflux is continued for one hour after completion of the addition, after which the reaction mixture is cooled to room temperature. The solution is decanted away from a small quantity of gum and the solvent is removed on a rotoevaporator. The resulting oil is dissolved in absolute ethanol, from which the title compound precipitates. m.p. 217°-220° C. IR (KBr) 1625, 1290, 1165, 1150 cm-1

Workup

  1. temperatureis heated from ambient temperature to 160° C. over one hour
  2. temperatureUpon cooling
  3. customliquids are removed in vacuo
  4. temperatureHeating
  5. temperatureat reflux
  6. additionafter completion of the addition
  7. customThe solution is decanted away from a small quantity of gum
  8. customthe solvent is removed on a rotoevaporator
  9. dissolutionThe resulting oil is dissolved in absolute ethanol, from which the title compound
  10. customprecipitates

Sources & evidence

ORD record
ord-b995ec928a7a49d3968c51767e759fbb
Source dataset
uspto-grants-1984_12
Patent number
US04490527

Reaction notes

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