1,3-Propanediamine → HCID 58727287, compound

HRID 502604Notes

Reaction equation

HRID 502604 reaction equation
Br[C:2]1[C:6]2[C:7]([CH3:11])=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][N:3]=1.[NH2:12][CH2:13][CH2:14][CH2:15][NH2:16]>CO.C(OCC)(=O)C>[CH3:11][C:7]1[C:6]2[C:2]([NH:12][CH2:13][CH2:14][CH2:15][NH2:16])=[N:3][S:4][C:5]=2[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 4281,3-PropanediamineHCID 574365593-Bromo-4-methylbenzo[d]isothiazole

Product 1

HCID 58727287HCID 58727287, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Bromo-4-methylbenzo[d]isothiazole (2.70 g, 11.84 mmol), and 1,3-diaminopropane (10.0 g, 135 mmol) in methanol (15 ml) was heated at 64° C. for 1.5 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The crude reaction mixture was diluted with ethyl acetate and washed successively with saturated aqueous sodium bicarbonate solution and brine. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Lyophilization of the crude sample in acetonitrile/water yielded N1-(4-methylbenzo[d]isothiazol-3-yl)propane-1,3-diamine sample. 1H NMR (300 MHz, DMSO-d6): 7.70 (d, 1H), 7.30 (t, 1H), 7.15 (dd, 1H), 6.58 (t, 1H), 3.47 (t, 2H), 2.96 (t, 2H), 2.73 (s, 3H), 1.92 (t, 2H), 1.56 ppm (m, 2H). MW=221 confirmed by LC-MS, tr=2.30 min (Method E) MH+=222.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude reaction mixture
  3. washwashed successively with saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9c163c4d6ef6402fbbdc054456318b50
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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