Hexamethylenediamine → HCID 131711208, compound

HRID 2419999Notes

Reaction equation

HRID 2419999 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[C:4]([Cl:10])[N:3]=1.[CH2:11]([NH2:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH2:17]>C1COCC1>[ClH:1].[Cl:8][C:7]1[C:2]([NH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][NH2:18])=[N:3][C:4]([Cl:10])=[C:5]([Cl:9])[CH:6]=1

Participants

4

Reactant 2

HCID 16402HexamethylenediamineHCID 169902,3,5,6-Tetrachloropyridine

Product 1

HCID 131711208HCID 131711208, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

24.2 grams (0.112 mole) of 2,3,5,6-tetrachloropyridine was added portionwise to a stirring solution of 1,6-hexanediamine (23.2 grams; 0.2 mole) in 300 ml. of THF. The mixture was stirred overnight at room temperature, then evaporated to dryness under reduced pressure. A solution of the residual material in water was made alkaline with K2CO3 and extracted with CH2Cl2. The organic layer was dried and evaporated to dryness and the residue dissolved in diethyl ether. Acidification with hydrogen chloride (in ether) precipitated 24.6 grams (66% of theory) of the title compound, a white solid melting at 124°-5° C.:

Workup

  1. customevaporated to dryness under reduced pressure
  2. extractionextracted with CH2Cl2
  3. customThe organic layer was dried
  4. customevaporated to dryness
  5. dissolutionthe residue dissolved in diethyl ether
  6. customAcidification with hydrogen chloride (in ether) precipitated 24.6 grams (66% of theory) of the title compound

Sources & evidence

ORD record
ord-a103db370d844bd9ba2915e63788186b
Source dataset
uspto-grants-1978_08
Patent number
US04108859

Reaction notes

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