Hydrochloric Acid → HCID 68508110, compound

HRID 1256893Notes

Reaction equation

HRID 1256893 reaction equation
[CH:1]1([C:4](O)=O)[CH2:3][CH2:2]1.[CH3:7][C:8]1([CH3:16])[O:15][C:13](=[O:14])[CH2:12][C:10](=[O:11])[O:9]1.CCN=C=NCCCN(C)C.Cl.Cl>C(Cl)Cl.CN(C)C1C=CN=CC=1.O>[CH:1]1([CH2:4][CH:12]2[C:13](=[O:14])[O:15][C:8]([CH3:16])([CH3:7])[O:9][C:10]2=[O:11])[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 15655Cyclopropanecarboxylic acidHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 68508110HCID 68508110, compoundYield 65.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of cyclopropanecarboxylic acid (17.2 g) in methylene chloride (800 mL) were added Meldrum's acid (28.8 g), WSCI.HCl (42.2 g) and 4-dimethylaminopyridine (39.1 g), and the mixture was stirred at room temperature for 18 hr. Water and then hydrochloric acid were added to acidify the reaction mixture, and the aqueous layer was removed by partitioning. Under ice-cooling, acetic acid (114 mL) and then sodium borohydride (18.9 g) were added slowly to the organic layer, and the mixture was stirred at room temperature for 3 days. Water and then hydrochloric acid were added to the reaction mixture, and the aqueous layer was removed by partitioning. The organic layer was concentrated to give a yellow powder. This was washed with ether/hexane to give the title compound (25.8 g) as a yellow powder.

Workup

  1. customthe aqueous layer was removed
  2. customby partitioning
  3. temperatureUnder ice-cooling
  4. additionacetic acid (114 mL) and then sodium borohydride (18.9 g) were added slowly to the organic layer
  5. stirringthe mixture was stirred at room temperature for 3 days
  6. additionWater and then hydrochloric acid were added to the reaction mixture
  7. customthe aqueous layer was removed
  8. customby partitioning
  9. concentrationThe organic layer was concentrated
  10. customto give a yellow powder
  11. washThis was washed with ether/hexane

Sources & evidence

ORD record
ord-3d189f770c8d43378194de7bede8cedd
Source dataset
uspto-grants-2013_06
Patent number
US08461209B2

Reaction notes

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