1,3-Propanediamine → HCID 178526631, compound

HRID 1398827Notes

Reaction equation

HRID 1398827 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]=[C:12](Cl)Cl.[CH2:15]([NH2:19])[CH2:16][CH2:17][NH2:18]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]=[C:12]1[NH:19][CH2:15][CH2:16][CH2:17][NH:18]1

Participants

4

Reactant 2

HCID 4281,3-PropanediamineHCID 86632875(2-Chloro-5-nitrophenyl)carbonimidic dichloride

Product 1

HCID 178526631HCID 178526631, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
7.5 °C

Procedure

(2-Chloro-5-nitrophenyl)carbonimidic dichloride (35.5 g, 140 mmol) was dissolved in tetrahydrofuran (135 mL). The solution was added dropwise within 30 min to a solution of 1,3-propanediamine (58 mL, 700 mmol) in tetrahydrofuran (335 mL) which was kept at 5-10° C. The reaction mixture was stirred for 1 h at 5-10° C. another 2 hr at room temperature. The suspension was filtered, and washed with tetrahydrofuran. The filtrate was concentrated in vacuo. The residue was taken up in water, filtered, and washed with water and diisopropyl ether. After drying at 50° C. under vacuum, the title compound (35.0 g, 137.4 mmol, 98%) was obtained as yellow crystals.

Workup

  1. customwas kept at 5-10° C
  2. filtrationThe suspension was filtered
  3. washwashed with tetrahydrofuran
  4. concentrationThe filtrate was concentrated in vacuo
  5. filtrationfiltered
  6. washwashed with water and diisopropyl ether
  7. customAfter drying at 50° C. under vacuum

Sources & evidence

ORD record
ord-2cef5a2b49e2405890788205e54880ef
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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