Putrescine → HCID 178526630, compound

HRID 1628472Notes

Reaction equation

HRID 1628472 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]([NH2:20])[CH2:16][CH2:17][CH2:18][NH2:19]>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:20][CH2:15][CH2:16][CH2:17][CH2:18][NH:19]1

Participants

4

Reactant 2

HCID 1045PutrescineHCID 86632875(2-Chloro-5-nitrophenyl)carbonimidic dichloride

Product 1

HCID 178526630HCID 178526630, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
7.5 °C

Procedure

(2-Chloro-5-nitrophenyl)carbonimidic dichloride (17.8 g, 70.0 mmol) was dissolved in tetrahydrofuran (68 mL). The solution was added dropwise within 30 min to a solution of 1,4-butanediamine (30.9 g, 350 mmol) in tetrahydrofuran (168 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 disopropyl ether. After drying at 50° C. under vacuum, the title compound (8.9 g, 33.4 mmol, 48%) was obtained as a yellow amorphous.

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 disopropyl ether
  7. customAfter drying at 50° C. under vacuum

Sources & evidence

ORD record
ord-7c27607417e64644b6c4df25daa4c4b6
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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