Pyridine → Chloride

HRID 983757Notes

Reaction equation

HRID 983757 reaction equation
[C:1]1(=[O:8])[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9](Cl)(=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([Cl:16])=[O:15].[N:19]1C=CC=[CH:21][CH:20]=1.[O:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>>[C:9]([CH:20]1[NH:19][C:26](=[O:25])[CH2:27][CH2:28][CH2:29][CH2:21]1)(=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([CH:6]1[NH:7][C:1](=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1)=[O:15].[Cl-:16]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7768CaprolactamHCID 8028TetrahydrofuranHCID 61034Adipoyl chloride

Product 2

HCID 312ChlorideHCID 22556249HCID 22556249, compound

Procedure

The adipoylbiscaprolactam (ABC) chain extender compound used in the following examples was prepared by dissolving 136 grams of caprolactam (1.2 moles) in 500 ml tetrahydrofuran (THF) in a 2 liter Erlenmeyer flask, cooling the resulting solution in an ice bath to below 5° C., and slowly adding 100 grams of adipoyl chloride (0.55 mole) with stirring. The temperature was maintained below 5° C. 200 ml of pyridine was added to the stirred solution to form a precipitate of ABC and pyridinum chloride. The mixture was stirred for ½ hour below 5° C., then heated to boiling for 30 minutes, followed by pouring the hot solution into a 3 gallon (13.5 liter) bucket half filled with a 50/50 mixture of water and ice with vigorous stirring. The ABC precipitates and all other ingredients stay in solution. Solid ABC (155.8 grams) was collected by suction filtration.

Workup

  1. customwas prepared
  2. temperaturecooling the resulting solution in an ice bath to below 5° C.
  3. temperatureThe temperature was maintained below 5° C

Sources & evidence

ORD record
ord-97a57f91cdcb46378c5df43db1802c13
Source dataset
uspto-grants-2005_03
Patent number
US06866930B2

Reaction notes

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