Pyridine → 2,3-Dihydroxypropyl-4-hexadecylaminobenzamide

HRID 2163776Notes

Reaction equation

HRID 2163776 reaction equation
Cl.[CH2:2]([NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=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[CH2:36][CH:37]([OH:40])[CH2:38][OH:39].[N:41]1C=CC=CC=1>CN(C)C1C=CN=CC=1.C(COC)OC>[OH:40][CH:37]([CH2:38][OH:39])[CH2:36][C:21]1[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:27]=[CH:26][C:22]=1[C:23]([NH2:41])=[O:25]

Participants

8

Reactant 5

HCID 1049PyridineHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 735613-Amino-1,2-propanediolHCID 70506019HCID 70506019, compound

Product 1

HCID 204373882,3-Dihydroxypropyl-4-hexadecylaminobenzamide

Reagents, catalysts & solvents 2

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

Procedure

A slurry of 8.0 g. of 4-(hexadecylamino)benzoic acid hydrochloride in 175 ml. of CH2Cl2 and 50 ml. of glyme containing 10 ml. of thionyl chloride was heated at reflux for 2 hours. The clear solution was concentrated in vacuo giving 9.5 g. of an amber oil. This oil was diluted with 50 ml. of pyridine containing 0.1 g. of 4-dimethylaminopyridine and 9.1 g. of 3-amino-1,2-propandiol. The reaction was stirred for two days at room temperature. The solution was partitioned between ether and water. The water phase was extracted twice more with 100 ml. of chloroform and ether. The combined organic layer was extracted with water, dried over MgSO4 and evaporated to a tacky solid. The solid was recrystallized from acetone-water and a second time from benzene. A small sample was recrystallized from acetonitrile, m.p. 121°-122° C.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationThe clear solution was concentrated in vacuo
  3. customgiving 9.5 g
  4. additionThis oil was diluted with 50 ml
  5. customThe solution was partitioned between ether and water
  6. extractionThe water phase was extracted twice more with 100 ml
  7. extractionThe combined organic layer was extracted with water
  8. dry with materialdried over MgSO4
  9. customevaporated to a tacky solid
  10. customThe solid was recrystallized from acetone-water
  11. customA small sample was recrystallized from acetonitrile, m.p. 121°-122° C.

Sources & evidence

ORD record
ord-e56e52f8e439426ca5dc7ce3590f707e
Source dataset
uspto-grants-1979_01
Patent number
US04136256

Reaction notes

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