Pyridine → HCID 20482586, compound

HRID 648329Notes

Reaction equation

HRID 648329 reaction equation
O[CH:2]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=1.N1C=CC=CC=1.S(Cl)([Cl:38])=O>C(Cl)(Cl)Cl>[Cl:38][CH:2]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 20482486HCID 20482486, compound

Product 1

HCID 20482586HCID 20482586, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 10 g. of ethyl 4-(6-hydroxyhexadecylamino)benzoate and 2.4 ml. of pyridine in 50 ml. of chloroform is treated with 2.0 ml. of thionyl chloride, stirred under reflux for 1 hour, washed with 1 N hydrochloric acid and saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and evaporated. The residue is crystallized from aqueous ethanol to yield the product as a white solid.

Workup

  1. temperatureunder reflux for 1 hour
  2. washwashed with 1 N hydrochloric acid and saturated aqueous sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue is crystallized from aqueous ethanol

Sources & evidence

ORD record
ord-c943a0ffe10b452fa4dc77fb38a248b3
Source dataset
uspto-grants-1983_10
Patent number
US04411903

Reaction notes

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