Pyridine → HCID 19014751, compound

HRID 248039Notes

Reaction equation

HRID 248039 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH2:14]([O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C(Cl)Cl.C(Cl)(Cl)Cl.O>[C:2]1([NH:1][C:33](=[O:34])[C:32]2[CH:31]=[CH:30][C:29]([O:28][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:37][CH:36]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 6115AnilineHCID 9998158Benzoyl chloride, 4-(tetradecyloxy)-

Product 1

HCID 19014751HCID 19014751, compoundYield 99.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 7.02 g of aniline and 4.48 g of pyridine in 200 ml of methylene chloride is added 20 g of product from Example 3. The reaction is stirred at room temperature for 2 hours; diluted with chloroform and water and heated to dissolve the solids. The layers are separated and the organic layer is washed with hot dilute hydrochloric acid. The organic layer is dried, concentrated in vacuo and the residue is recrystallized from chloroform/hexane to give 23.1 g of the desired product.

Workup

  1. temperatureheated
  2. dissolutionto dissolve the solids
  3. customThe layers are separated
  4. washthe organic layer is washed with hot dilute hydrochloric acid
  5. customThe organic layer is dried
  6. concentrationconcentrated in vacuo
  7. customthe residue is recrystallized from chloroform/hexane

Sources & evidence

ORD record
ord-5b7e8ddf8c2b4a3893c1f63a3a573560
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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