2-Morpholinoethanol → HCID 21327982, compound

HRID 614526Notes

Reaction equation

HRID 614526 reaction equation
[CH:1]1[N:9]2[C:4]([CH2:5][O:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)=[N:3][C:2]=1[C:14](Cl)=[O:15].[OH:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>ClCCl>[CH:1]1[N:9]2[C:4]([CH2:5][O:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)=[N:3][C:2]=1[C:14]([O:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[O:15]

Participants

4

Reactant 2

HCID 611632-MorpholinoethanolHCID 14067389HCID 14067389, compound

Product 1

HCID 21327982HCID 21327982, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

1.0 g (0.0043 mole) of 4H-imidazo-[2,1-c][1,4]-benzoxazine-2-carbonyl chloride was suspended in dry dichloromethane and 1.31 g (0.01 mole) of N-(2-hydroxyethyl)-morpholine was added thereto. The mixture was warmed at 50° C. for two hours and thin layer chromatography then indicated only a small quantity of starting material remained. The mixture was then washed with water, dried and evaporated. The residue was chromatographed on a silica column using ethyl acetate as eluant. The product thus obtained was finally crystallized from ether to obtain 0.6 g (43% yield) of 2-morpholinoethyl 4H-imidazo-[2,1-c][1,4]-benzoxazine-2-carboxylate with a melting point of 142°-3° C.

Workup

  1. washThe mixture was then washed with water
  2. customdried
  3. customevaporated
  4. customThe residue was chromatographed on a silica column
  5. customThe product thus obtained
  6. customwas finally crystallized from ether

Sources & evidence

ORD record
ord-e378be2b31214079a8625b2864df2973
Source dataset
uspto-grants-1979_03
Patent number
US04145419

Reaction notes

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