Pyridine → HCID 9983353, compound

HRID 653789Notes

Reaction equation

HRID 653789 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].N1C=CC=CC=1.[CH2:16]([O:32][C:33]1[CH:43]=[CH:42][C:36]([O:37][CH2:38][C:39](Cl)=[O:40])=[CH:35][CH:34]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:16]([O:32][C:33]1[CH:34]=[CH:35][C:36]([O:37][CH2:38][C:39]([NH:1][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH2:4][OH:5])=[O:40])=[CH:42][CH:43]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 3

HCID 1049PyridineHCID 214392-Aminobenzyl alcoholHCID 104317244-Hexadecyloxyphenoxyacetic chloride

Product 1

HCID 9983353HCID 9983353, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.36 g of 0-aminobenzyl alcohol and 2.69 g of pyridine in 60 ml of methylene chloride is added dropwise with stirring over 40 minutes a solution of 3.5 g of 4-hexadecyloxyphenoxyacetyl chloride in 40 ml of methylene chloride. Stirring is continued at room temperature for 4 hours. The mixture is diluted with chloroform and heated to dissolve the solids, washed with water and dilute hydrochloric acid. The organic layer is dried and evaporated to a residue which is crystallized from carbon tetrachloride to give 3.9 g of the desired product as a white solid, m.p. 128°-131° C.

Workup

  1. temperatureheated
  2. dissolutionto dissolve the solids
  3. washwashed with water and dilute hydrochloric acid
  4. customThe organic layer is dried
  5. customevaporated to a residue which
  6. customis crystallized from carbon tetrachloride

Sources & evidence

ORD record
ord-67d1102cf5a4499f8f4a3e5c010121e5
Source dataset
uspto-grants-1992_07
Patent number
US05128351

Reaction notes

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