Dimethylamine → HCID 178439569, compound

HRID 27341Notes

Reaction equation

HRID 27341 reaction equation
[CH:1]([C:4]1([CH3:18])[N:8]2[C:9](=[O:16])[C:10]3[C:15]([C:7]2=[N:6][C:5]1=[O:17])=[CH:14][CH:13]=[CH:12][CH:11]=3)([CH3:3])[CH3:2].[CH3:19][NH:20][CH3:21]>O1CCCC1>[CH:1]([C:4]1([CH3:18])[NH:8][C:7]([C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]([N:20]([CH3:21])[CH3:19])=[O:16])=[N:6][C:5]1=[O:17])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 27292473-isopropyl-3-methyl-3H-imidazo[2,1-a]isoindole-2,5-dione

Product 1

HCID 178439569HCID 178439569, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a cold solution of 180 g of 3-isopropyl-3-methyl-5H-imidazo[2,1-a]isoindole-2(3H),5-dione in 300 ml of dry tetrahydrofuran in a pressure bottle is added 68 g of dimethylamine. The bottle is sealed and the mixture heated to 50° C. with stirring for 16 hours. The mixture is cooled, and the contents of the bottle transferred to a flask. The solvent is then removed in vacuo. The crystalline residue is then suspended in ether, filtered, washed with ether, and airdried to give 195 g of o-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-N,N-dimethylbenzamide, melting point 144°-146° C. This product is recrystallized from acetonitrile to give an analytically pure product, melting point 147°-150° C.

Workup

  1. customThe bottle is sealed
  2. temperatureThe mixture is cooled
  3. customthe contents of the bottle transferred to a flask
  4. customThe solvent is then removed in vacuo
  5. filtrationfiltered
  6. washwashed with ether

Sources & evidence

ORD record
ord-fdf6817cae504ef58d3b12591af00b49
Source dataset
uspto-grants-1980_09
Patent number
US04221586

Reaction notes

Loading…