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

HRID 964525Notes

Reaction equation

HRID 964525 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-18ce53a4422645bab3d40d98c3cc44a9
Source dataset
uspto-grants-1998_06
Patent number
US05770584

Reaction notes

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