Trimethylamine → HCID 20510897, compound

HRID 1758132Notes

Reaction equation

HRID 1758132 reaction equation
[Br:1][CH2:2][C:3]1[N:7](C(=[O:10])C)[C:6](=[O:11])[N:5](C(=O)C)[C:4]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16].[CH3:20][N:21]([CH3:23])[CH3:22]>O1CCCC1>[OH2:10].[Br-:1].[CH2:18]([O:17][C:15]([C:4]1[NH:5][C:6](=[O:11])[NH:7][C:3]=1[CH2:2][N+:21]([CH3:23])([CH3:22])[CH3:20])=[O:16])[CH3:19]

Participants

4

Reactant 2

HCID 1146TrimethylamineHCID 12850293HCID 12850293, compound

Product 1

HCID 20510897HCID 20510897, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 10.4 g of crude ethyl 5-(bromomethyl)-1,3-diacetyl-2,3-dihydro-2-oxo-1H-imidazole-4-carboxylate in 100 ml of dry tetrahydrofuran, cooled in an ice bath under argon, there is added gaseous trimethylamine for 7 minutes. The mixture is stirred at 0° C. for 15 minutes and then evaporated to dryness. To the residue is added 50 ml of 31% hydrogen bromide in acetic acid and the mixture is warmed briefly on a steam bath to about 50° C. to bring about dissolution. It is then allowed to stand at room temperature for 1 hour before it is evaporated to dryness. Water (50 ml) is added to the residue and the resultant aqueous mixture is washed with methylene chloride, treated with charcoal, filtered through diatomaceous earth, and evaporated to dryness. The resultant residue is crystallized from a mixture of ethanol and ethyl acetate (1:3) and then recrystallized from ethanol to give 5-(ethoxycarbonyl)-2,3-dihydro-N,N,N-trimethyl-2-oxo-1H-imidazole-4-methanaminium bromide monohydrate melting at about 199°-200° C. (dec.). This compound has the following structural formula: ##STR7##

Workup

  1. customevaporated to dryness
  2. additionTo the residue is added 50 ml of 31% hydrogen bromide in acetic acid
  3. temperaturethe mixture is warmed briefly on a steam bath to about 50° C.
  4. dissolutiondissolution
  5. waitto stand at room temperature for 1 hour before it
  6. customis evaporated to dryness
  7. additionWater (50 ml) is added to the residue
  8. washthe resultant aqueous mixture is washed with methylene chloride
  9. additiontreated with charcoal
  10. filtrationfiltered through diatomaceous earth
  11. customevaporated to dryness
  12. customThe resultant residue is crystallized from a mixture of ethanol and ethyl acetate (1:3)
  13. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6de5c7e30ac249bb8d1b66349f245fad
Source dataset
uspto-grants-1983_02
Patent number
US04371737

Reaction notes

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