1,3-Propanediamine → HCID 57436514, compound

HRID 502584Notes

Reaction equation

HRID 502584 reaction equation
[C:1]([NH:5][S:6]([C:9]1[C:17]2[S:16][N:15]=[C:14](Cl)[C:13]=2[CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[NH2:20][CH2:21][CH2:22][CH2:23][NH2:24]>>[NH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:14]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([S:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:8])=[O:7])[C:17]=2[S:16][N:15]=1

Participants

4

Reactant 3

HCID 4281,3-PropanediamineHCID 962WaterHCID 58726915HCID 58726915, compound

Product 1

HCID 57436514HCID 57436514, compound

Procedure

A solution of N-tert-butyl-3-chlorobenzo[d]isothiazole-7-sulfonamide (260 mg, 0.85 mmol) in 1,3-diaminopropane (1 mL) was allowed to stir at room temperature for 3h. The dark brown reaction mixture was then poured over water (10 mL), extracted with ethyl acetate and the combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 3-(3-aminopropylamino)-N-tert-butylbenzo[d]isothiazole-7-sulfonamide (271 mg) as a pale yellow solid. 1H NMR (300 MHz, CD3OD): 8.17 (dd, 1H), 8.01 (dd, 1H), 7.55 (t, 1H), 3.58 (t, 2H), 2.81 (t, 2H), 1.86-1.95 (m, 2H), 1.17 ppm (s, 9H). MW=342 confirmed by LC-MS, tr=7.95 min (Method Y) MH+=343.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e65b876e76b4a898fc34da376f267fc
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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