Morpholine → Morpholine, 4-(isocyanoacetyl)-

HRID 1423869Notes

Reaction equation

HRID 1423869 reaction equation
[N+:1]([CH2:3][C:4](OC)=[O:5])#[C-:2].[NH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1>>[N+:1]([CH2:3][C:4]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:5])#[C-:2]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 547815Methyl isocyanoacetate

Product 1

HCID 6455475Morpholine, 4-(isocyanoacetyl)-Yield 58%

Procedure

Prepared in accordance with Method B with methyl isocyanoacetate (2.51 g, 25.30 mmol) and morpholine (3.30 mL, 38.05 mmol). The reaction mixture was stirred 24 h at RT and then concentrated. The residue was dissolved in dichloromethane (50 mL) and the organic layer was washed with 10% aqueous citric acid (2×25 mL), dried over MgSO4, filtered and evaporated. 2-Isocyano-1-morpholinoethanone SLA 07118 was obtained as a brown oil (2.28 g, 58% yield).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  3. washthe organic layer was washed with 10% aqueous citric acid (2×25 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-303b536dbf55423fb1168644c2f6e458
Source dataset
uspto-grants-2015_01
Patent number
US08927589B2

Reaction notes

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