Ammonia → 4-(Hydroxymethyl)-1,4-dimethylimidazolidin-2-one

HRID 1025923Notes

Reaction equation

HRID 1025923 reaction equation
Cl.N[C:3]([CH3:9])([CH2:6]NC)[CH2:4][OH:5].[NH2:10][C:11]([NH2:13])=[O:12].N.Cl[CH2:16]Cl>>[OH:5][CH2:4][C:3]1([CH3:9])[CH2:6][N:13]([CH3:16])[C:11](=[O:12])[NH:10]1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 1176UreaHCID 6344DichloromethaneHCID 866655492-Amino-2-methyl-3-(methylamino)propan-1-ol hydrochloride

Product 1

HCID 675087194-(Hydroxymethyl)-1,4-dimethylimidazolidin-2-oneYield 45%

Procedure

In a round bottom flask, a mixture of 2-amino-2-methyl-3-(methylamino)propan-1-ol hydrochloride (3.3 g, 21 mmol) and urea (1.26 g, 21 mmol) were heated in a 200° C. sand bath for 1 hour until ammonia gas ceased to evolve. The resultant mixture was suspended in dichloromethane and filtered to remove insoluble material. The organic solution was concentrated to 3.3 g of black solid and purified by column chromatography, eluting from silica gel with a gradient of 1-12% methanol in dichloromethane to give 1.3 g of desired product as a tan oil (45% yield). 1H NMR (400 MHz, CDCl3) δ1.26 (s, 3H), 2.76 (s, 3H), 3.07-3.9 (d, J=8.8 Hz, 1H), 3.36-3.36 (d, J=8.8 Hz, 1H), 3.43-3.44 (d, J=2.1 Hz, 2H), 3.46 (s, 1H). 13C NMR (100 MHz, CDCl3/MeOD) δ 23.5, 30.1, 50.0, 55.7, 67.7, 161.9. LRMS (ESI/APCI): 145 [M+H]+.

Workup

  1. filtrationfiltered
  2. customto remove insoluble material
  3. concentrationThe organic solution was concentrated to 3.3 g of black solid
  4. custompurified by column chromatography
  5. washeluting from silica gel with a gradient of 1-12% methanol in dichloromethane

Sources & evidence

ORD record
ord-3cb9ac3469d141ac8d9862757c110f35
Source dataset
uspto-grants-2014_05
Patent number
US08729112B2

Reaction notes

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