1,3-Propanediamine → HCID 178526631, compound

HRID 1628474Notes

Reaction equation

HRID 1628474 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-fbdc7aab0f1542e282d1cda170c6c9f5
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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