3-Amino-1,2-propanediol → HCID 53324037, compound

HRID 1530863Notes

Reaction equation

HRID 1530863 reaction equation
C1(=O)NC(=O)CC1.[C:8]([OH:27])(=O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[NH2:28][CH2:29][CH:30]([OH:33])[CH2:31][OH:32]>C(#N)C.O>[OH:33][CH:30]([CH2:31][OH:32])[CH2:29][NH:28][C:8](=[O:27])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 2

HCID 735613-Amino-1,2-propanediolHCID 69746761HCID 69746761, compound

Product 1

HCID 53324037HCID 53324037, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of cis-9-octadecenoic acid succinimide (18.3 g, 48.2 mmol) in 50 ml of acetonitrile is added 1-amino-2,3-propanediol (4.4 g, 48.2 mmol) in 50 ml of H2O. After stirring for 12 hours at room temperature the acetonitrile is distilled off and the residue is extracted with ethyl acetate. The combined organic phases are extracted with saturated NaCl solution. The organic phase is dried with MgSO4, filtrated and concentrated. The residue is crystallized from isohexane. Yield: 87% of a colorless powder.

Workup

  1. distillationis distilled off
  2. extractionthe residue is extracted with ethyl acetate
  3. extractionThe combined organic phases are extracted with saturated NaCl solution
  4. dry with materialThe organic phase is dried with MgSO4
  5. filtrationfiltrated
  6. concentrationconcentrated
  7. customThe residue is crystallized from isohexane

Sources & evidence

ORD record
ord-be5d324203ad43c58e607c0cba142dea
Source dataset
uspto-grants-2001_03
Patent number
US06197759B1

Reaction notes

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