1,6-Dibromohexane → N(6-bromohexyl)-4-styrylpyridinium bromide

HRID 376472

Reaction equation

HRID 376472 reaction equation
[CH:1]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][Br:22]>C(OC(=O)C)C>[Br-:15].[Br:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N+:12]1[CH:13]=[CH:14][C:9]([CH:1]=[CH:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 123681,6-DibromohexaneHCID 1015764-(2-Phenylethenyl)pyridine

Product 1

HCID 70263189N(6-bromohexyl)-4-styrylpyridinium bromideYield 86.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.91 g of 4-styrylpyridine and 2.44 g of 1,6-dibromohexane in 15 ml of ethylacetate was stirred and refluxed for 3 hours then filtered while hot. The crystals obtained were washed with an additional portion of ethylacetate and dried in vacuo to give 1.84 g of N(6-bromohexyl)-4-styrylpyridinium bromide. λmax 343 nm (water). NMR (CDCl3, p.p.m.): 9.4 (d.,2H), 8.2 (d.,2H), 7.2-7.8 (m.,7H), 4.9(t.,2H), 3.35(T.,2H), 1.2-2.2 (br.m., 8H).

Workup

  1. temperaturerefluxed for 3 hours
  2. filtrationthen filtered while hot
  3. customThe crystals obtained
  4. washwere washed with an additional portion of ethylacetate
  5. customdried in vacuo

Sources & evidence

ORD record
ord-5ab54ae53c58483c91e4fd0fbabe4802
Source dataset
uspto-grants-2000_02
Patent number
US06020436

Linked notes

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