1,3-Propanediamine → HCID 57436513, compound

HRID 502581Notes

Reaction equation

HRID 502581 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[S:17][N:16]=[C:15](Cl)[C:14]=12)(=[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:15]1[C:14]2=[C:9]([S:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:8])=[O:7])[CH:10]=[CH:11][CH:12]=[C:13]2[S:17][N:16]=1

Participants

4

Reactant 3

HCID 4281,3-PropanediamineHCID 962WaterHCID 58727128HCID 58727128, compound

Product 1

HCID 57436513HCID 57436513, compound

Procedure

A solution of N-tert-butyl-3-chlorobenzo[d]isothiazole-4-sulfonamide (280 mg, 0.92 mmol) in 1,3-diaminopropane (1 mL) was allowed to stir at room temperature for 2.5 h. The reaction mixture was then poured over water (10 mL), extracted with ethyl acetate and the combined organic layers was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give, upon trituration with ethyl ether, 3-(3-aminopropylamino)-N-tert-butylbenzo[d]isothiazole-4-sulfonamide (257 mg) as an off-white solid. 1H NMR (300 MHz, CD3OD): 8.02 (d, 1H), 7.85 (d, 1H), 7.70 (t, 1H), 3.74 (t, 2H), 3.02 (t, 2H), 1.87-1.95 (m, 2H), 1.24 ppm (s, 9H). MW=342 confirmed by LC-MS, tr=8.22 min (Method Y) MH+=343.

Workup

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

Sources & evidence

ORD record
ord-6145664da76b4b258c5d48db76ddc9dc
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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