Water → 3-(N-n-Heptadecylcarbamoyl)oxypropan-1-ol

HRID 1285236Notes

Reaction equation

HRID 1285236 reaction equation
[CH2:1]([N:18]=[C:19]=[O:20])[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].O.C(Cl)(Cl)Cl.[CH2:26]([OH:30])[CH2:27][CH2:28][OH:29]>C(Cl)Cl>[CH2:1]([NH:18][C:19]([O:29][CH2:28][CH2:27][CH2:26][OH:30])=[O:20])[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]

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 104421,3-PropanediolHCID 135601031-Isocyanatoheptadecane

Product 1

HCID 135601043-(N-n-Heptadecylcarbamoyl)oxypropan-1-olYield 47.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a mixture of 5.7 g of 1,3-propanediol and 30 ml of methylene chloride is dissolved 5.0 g of n-heptadecyl isocyanate and the mixture is stirred at room temperature overnight. To the reaction mixture are added 20 ml each of water and chloroform, and the organic layer is taken and concentrated to dryness. Then, silica gel column chromatography is carried out [eluent: chloroform-water (97:3)] and the eluate is concentrated to dryness. The procedure provides 3.0 g of the above-indicated compound as colorless crystals.

Workup

  1. concentrationconcentrated to dryness
  2. concentrationthe eluate is concentrated to dryness

Sources & evidence

ORD record
ord-e64f399b4ade4a0283755353372f0bfe
Source dataset
uspto-grants-1986_01
Patent number
US04565865

Reaction notes

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