Dimethylamine → HCID 12952964, compound

HRID 2286242Notes

Reaction equation

HRID 2286242 reaction equation
[ClH:1].[Cl:2][CH2:3][CH2:4][CH:5]1[CH2:9][N:8]([CH3:10])[C:7](=[NH:11])[N:6]1[CH3:12].[CH3:13][NH:14][CH3:15].C[OH:17]>>[OH2:17].[ClH:2].[ClH:1].[NH:11]=[C:7]1[N:6]([CH3:12])[CH:5]([CH2:4][CH2:3][N:14]([CH3:15])[CH3:13])[CH2:9][N:8]1[CH3:10]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 887MethanolHCID 20542259HCID 20542259, compound

Product 1

HCID 12952964HCID 12952964, compoundYield 26%

Procedure

To 10.0 g (0.047 mole) of 4-(2-chloroethyl)-2-imino-1,3-dimethylimidazolidine hydrochloride was added 6.8 g (0.15 mole) of dimethylamine in 175 ml of methanol. The mixture was heated in a steel bomb at 100° C. for 15 hours. After concentrating in vacuo, the residue was partitioned between a dilute sodium carbonate solution and chloroform. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was dissolved in ethyl acetate and treated with ethereal HCl. The hydrochloride was recrystallized from ethanol twice, and weighed 3.2 g (26% yield); m.p. 210°-212° C.

Workup

  1. concentrationAfter concentrating in vacuo
  2. customthe residue was partitioned between a dilute sodium carbonate solution and chloroform
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. additiontreated with ethereal HCl
  8. customThe hydrochloride was recrystallized from ethanol twice

Sources & evidence

ORD record
ord-8bba306ccd2e4e54b5032ca7c589d8ac
Source dataset
uspto-grants-1982_04
Patent number
US04327108

Reaction notes

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