Stearoyl chloride → N-(2,3-dihydroxypropyl)stearamide

HRID 378224Notes

Reaction equation

HRID 378224 reaction equation
[NH2:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].[C:7](Cl)(=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>N1C=CC=CC=1.CN(C=O)C>[C:7]([NH:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5])(=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 2

HCID 8212Stearoyl chlorideHCID 735613-Amino-1,2-propanediol

Product 1

HCID 81787N-(2,3-dihydroxypropyl)stearamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a mechanically stirred solution of 3-amino-1,2-propanediol (32 g, 0.35 mol) in 100 mL of pyridine and 250 mL of DMF was added a solution of stearoyl chloride (100.0 g, 0.33 mol) in 150 mL of DMF. After stirring for 1 h, precipitation occurred and an additional 100 mL of DMF was added. After 2 h, the gelatinous mass was filtered, washed with water, and air dried. The solid was recrystallized successively from EtOH, isopropanol, and chloroform to give 74 g (63%) as a white powder (mp 111.5-113.5° C.). 1H-NMR: 0.86 (t, 3H, CH3), 1.25 (broad m, 28H, (CH2)14), 1.55 (m, 2H, NHCOCH2CH2), 2.20 (t, 2H NHCOCH2), 3.4 (m, 2H, CH2NH), 3.55 (d, 2H, CH2OH). 3.75 (m, 1H, CH), 5.8 (m, 1H, NH).

Workup

  1. customprecipitation
  2. additionan additional 100 mL of DMF was added
  3. waitAfter 2 h
  4. filtrationthe gelatinous mass was filtered
  5. washwashed with water, and air
  6. customdried
  7. customThe solid was recrystallized successively from EtOH, isopropanol, and chloroform

Sources & evidence

ORD record
ord-6f33d40f140f404487d84a49c4dad379
Source dataset
uspto-grants-2000_02
Patent number
US06030960

Reaction notes

Loading…