1,3-Propanediamine → N1-(benzo[d]isothiazol-3-yl)propane-1,3-diamine

HRID 502547Notes

Reaction equation

HRID 502547 reaction equation
Cl[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][N:3]=1.O.[CH2:12]([NH2:16])[CH2:13][CH2:14][NH2:15]>>[S:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:2]([NH:15][CH2:14][CH2:13][CH2:12][NH2:16])=[N:3]1

Participants

4

Reactant 3

HCID 4281,3-PropanediamineHCID 962WaterHCID 5981903-Chloro-1,2-benzisothiazole

Product 1

HCID 57436551N1-(benzo[d]isothiazol-3-yl)propane-1,3-diamine

Conditions

Temperature
80 °C

Procedure

3-Chlorobenzo[d]isothia-zole (300 mg, 3.0 mmol) was dissolved in propane-1,3-diamine (3 mL) and heated at 80° C. for 3 h. The reaction mixture was cooled to room temperature, poured into water and extracted with ethyl acetate. The organic extract was dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under reduced pressure to yield N1-(benzo[d]isothiazol-3-yl)propane-1,3-diamine as a yellow solid, (530 mg). 1H NMR (300 MHz, CDCl3): 7.8 (m, 1H), 7.7 (m, 1H), 7.5 (m, 2H), 7.3 (m, 1H), 3.7 (m, 2H), 2.9 (t, 2H), 1.9 ppm (m, 2H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-8633bfd3380b4410a0f9fd00f75cad90
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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