Pyridine → HCID 20525731, compound

HRID 1702696Notes

Reaction equation

HRID 1702696 reaction equation
Cl.[CH2:2]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([OH:28])=O)=[CH:21][CH:20]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(Cl)Cl.S(Cl)(Cl)=O.N[CH2:37][CH:38]([OH:41])[CH2:39][OH:40].[N:42]1C=CC=CC=1>CN(C)C1C=CN=CC=1.C(COC)OC>[OH:41][CH:38]([CH2:39][OH:40])[CH2:37][CH:25]([C:22]1[CH:21]=[CH:20][C:19]([NH:18][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:24][CH:23]=1)[C:26]([NH2:42])=[O:28]

Participants

8

Reactant 5

HCID 1049PyridineHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 735613-Amino-1,2-propanediolHCID 70544527HCID 70544527, compound

Product 1

HCID 20525731HCID 20525731, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A slurry of 8.0 g. of 4-(hexadecylamino)phenylacetic acid hydrochloride in 175 ml. of methylene chloride and 50 ml. of glyme containing 10 ml. of thionyl chloride is heated at reflux for 2 hours. The clear solution is concentrated in vacuo giving 9.5 g. of an amber oil. This oil is dilutd with 50 ml. of pyridine containing 0.1 g. of 4-dimethylaminopyridine and 9.1 g. of 3-amino-1,2-propanediol. The reaction is stirred for two days at room temperature. The solution is partitioned between ether and water. The water phase is extracted twice more with 100 ml. of chloroform and ether. The combined organic layer is extracted with water, dried over magnesium sulfate and evaporated to a tacky solid. The solid is recrystallized from acetone-water and then from benzene.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationThe clear solution is concentrated in vacuo
  3. customgiving 9.5 g
  4. customThe solution is partitioned between ether and water
  5. extractionThe water phase is extracted twice more with 100 ml
  6. extractionThe combined organic layer is extracted with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to a tacky solid
  9. customThe solid is recrystallized from acetone-water

Sources & evidence

ORD record
ord-0e2afd7a7e754c7ea28e8d87768a97bf
Source dataset
uspto-grants-1982_09
Patent number
US04348399

Reaction notes

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