Sarcosine → HCID 20463711, compound

HRID 325578Notes

Reaction equation

HRID 325578 reaction equation
Br[CH2:2][C:3](Br)=[O:4].[NH:6]([CH2:8][C:9]([OH:11])=[O:10])[CH3:7].C(N(CC)CC)C>C1COCC1>[CH3:7][N:6]1[C:3](=[O:4])[CH2:2][O:10][C:9](=[O:11])[CH2:8]1

Participants

5

Reactant 3

HCID 1088SarcosineHCID 8471TriethylamineHCID 61147Bromoacetyl bromide

Product 1

HCID 20463711HCID 20463711, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

Bromacetyl bromide (202 g, 1.0 moles) is dissolved in THF (400 ml) and rapidly added to a cooled (15° C.), vigorously stirred sarcosine (178.2, 2.0 moles)-THF (900 ml) mixture. After two hours of thorough mixing at room temperature the reaction mixture is filtered. Triethylamine (101 g, 1.0 moles) is added to the filtrate. This reaction mixture is stirred at 50° C. for 0.25 hours and then filtered. Evaporation of this filtrate's solvent produces roughly 80 g of crude, liquid N-methyl-2,5-morpholinedione. Vacuum distillation of this oil yields 60 g of N-methyl-2,5-morpholinedione (B.P. 114°-116° C. at 0.1 mm, ND23 =1.4967). Proton NMR analysis of the distillate shows chemical shifts at 2.952, 2.985, 3.94, 4.16, and 4.74 PPM. Elemental analysis of the compound is as follows--calculated for C5H7NO3 : C, 46.50; H, 5.48; N, 10.84; O, 37.17%. Found: C, 46.78; H, 5.80; N, 11.16; O, 36.47%.

Workup

  1. additionrapidly added to
  2. additionAfter two hours of thorough mixing at room temperature the reaction mixture
  3. filtrationis filtered
  4. filtrationfiltered
  5. customEvaporation of this filtrate's solvent

Sources & evidence

ORD record
ord-39ca6936f3674ea08051346c8dab4242
Source dataset
uspto-grants-1984_04
Patent number
US04441496

Reaction notes

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