3-Chloro-1,2-propanediol → HCID 20378122, compound

HRID 2051856Notes

Reaction equation

HRID 2051856 reaction equation
ClCC(O)CO.CN.CO.Cl.[CH3:12][NH:13][CH2:14][CH:15]([OH:18])[CH2:16][OH:17].[Cl:19][CH2:20][CH2:21][N:22]=[C:23]=[O:24]>CO.C(N(CC)CC)C>[Cl:19][CH2:20][CH2:21][NH:22][C:23]([N:13]([CH3:12])[CH2:14][CH:15]([OH:18])[CH2:16][OH:17])=[O:24]

Participants

7

Reactant 4

HCID 72903-Chloro-1,2-propanediolHCID 160352-Chloroethyl isocyanateHCID 20378142HCID 20378142, compoundHCID 57454252Monomethylamine methanol

Product 1

HCID 20378122HCID 20378122, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 3.3 g of 3-chloro-1,2-dihydroxy-n-propane and 20 ml of 30% methylamine-methanol solution is allowed to stand at room temperature for 3 days. The reaction mixture is condensed to dryness under reduced pressure, whereby 4.2 g of N-methyl-2,3-dihydroxy-n-propylamine hydrochloride are obtained as a crude product. 4.2 g of said crude product and 3 g of triethylamine are dissolved in 30 ml of methanol. To the solution, 3.2 g of 2-chloroethyl isocyanate are added dropwise to the solution at 0° to 5° C. The solution is stirred at room temperature for 2 hours. Then, the reaction solution is condensed under reduced pressure and the residue thus obtained is purified by silica gel chromatography (Solvent: chloroform-ethyl acetate-methanol(3:1:1)). 3.5 g of 1-(2-chloroethyl)-3-methyl-3-(2,3-dihydroxy-n-propyl)urea are obtained as a colorless oil.

Workup

  1. customare obtained as a crude product
  2. customcondensed under reduced pressure
  3. customthe residue thus obtained
  4. customis purified by silica gel chromatography (Solvent: chloroform-ethyl acetate-methanol(3:1:1))

Sources & evidence

ORD record
ord-b82007a69a2147eaa96c3241c3a5645d
Source dataset
uspto-grants-1980_01
Patent number
US04182757

Reaction notes

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