Ethanolamine → HCID 20061447, compound

HRID 1085294Notes

Reaction equation

HRID 1085294 reaction equation
[CH2:1](Br)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:10]([CH2:12][NH2:13])[OH:11].C(O)(C)C.Cl[C:19]1[N:24]([CH3:25])[C:23](=[O:26])[N:22]([CH3:27])[C:21](=[O:28])[CH:20]=1>CN(C)C=O.C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:25][N:24]1[C:19]([N:13]([CH2:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:12][CH2:10][OH:11])=[CH:20][C:21](=[O:28])[N:22]([CH3:27])[C:23]1=[O:26]

Participants

8

Reactant 4

HCID 700EthanolamineHCID 3776IsopropanolHCID 7666Phenethyl bromideHCID 814426-Chloro-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 20061447HCID 20061447, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
110 °C

Procedure

A mixture consisting of 3 ml of phenethyl bromide, 13 ml of ethanolamine and 15 ml of isopropanol was heated for 2 hours under reflux. After allowing the reaction mixture to cool down, 50 ml of chloroform were added. The thus-prepared mixture was washed with water and then concentrated to obtain an oily substance. To the oily substance, 3.5 g of 6-chloro-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione and 3.3 ml of triethylamine were added. The resultant mixture was dissolved in 15 ml of dimethylformamide and stirred at 110° C. for 4 hours. The solution was cooled down to room temperature, followed by the addition of 150 ml of chloroform. The resultant chloroform solution was washed with water and then concentrated to obtain an oily substance. By crystallizing the oily substance from ether, 4.1 g of 1,3-dimethyl-6-[N-(2-hydroxyethyl)-2-phenylethylamino]-2,4(1H,3H)-pyrimidinedione were obtained as crystals.

Workup

  1. temperaturewas heated for 2 hours
  2. temperatureunder reflux
  3. temperatureto cool down
  4. washThe thus-prepared mixture was washed with water
  5. concentrationconcentrated
  6. customto obtain an oily substance
  7. temperatureThe solution was cooled down to room temperature
  8. washThe resultant chloroform solution was washed with water
  9. concentrationconcentrated
  10. customto obtain an oily substance
  11. customBy crystallizing the oily substance from ether

Sources & evidence

ORD record
ord-7d49dc7392c8479c9dd0464fd332e39a
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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