Hydrochloric Acid → HCID 15906535, compound

HRID 279492Notes

Reaction equation

HRID 279492 reaction equation
[CH3:1][C:2]([C@H:4]1[CH2:9][C@H:8]2[O:10][C@@:7]2([CH3:11])[CH2:6][CH2:5]1)=[CH2:3].[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1.Cl.[K+].[Br-]>C(OCC)C.C(Cl)(Cl)Cl.O>[N:12]1([C@H:8]2[CH2:9][C@H:4]([C:2]([CH3:1])=[CH2:3])[CH2:5][CH2:6][C@:7]2([CH3:11])[OH:10])[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 253877Potassium BromideHCID 449290(+)-trans-Limonene oxide

Product 1

HCID 15906535HCID 15906535, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

To (R)-(+)-limonene oxide (6.88 mmol, 1.047 g, 1.13 mL) were added 6 mL of deionized water and imidazole (21 mmol, 1.43 g) at 25° C. A reflux condenser was attached and the flask was set in an oil bath that was heated to 100° C. After 5.0 h at 100° C., the reaction mixture was cooled to 25° C., acidified with 12M hydrochloric acid, and extracted with diethyl ether (7×30 mL). The aqueous layer was cooled to 0° C. and treated with solid sodium hydroxide until the solution was strongly basic to litmus (pH 10). The solution was extracted with methylene chloride (10×30 mL) and the combined extracts were dried. The solvent was removed in vacuo leaving a semi-solid material that was taken up in hot diethyl ether. The solution was cooled to give a white, crystalline solid, mp 126-128° C.; [α]25D=+11.4 (c=3.5 in CHCl3); IR (KBr) 3210.0, 2850.0 cm−1.

Workup

  1. customA reflux condenser was attached
  2. customthe flask was set in an oil bath
  3. temperaturethe reaction mixture was cooled to 25° C.
  4. extractionextracted with diethyl ether (7×30 mL)
  5. temperatureThe aqueous layer was cooled to 0° C.
  6. additiontreated with solid sodium hydroxide until the solution
  7. extractionThe solution was extracted with methylene chloride (10×30 mL)
  8. customthe combined extracts were dried
  9. customThe solvent was removed in vacuo
  10. customleaving a semi-solid material that
  11. temperatureThe solution was cooled
  12. customto give a white, crystalline solid, mp 126-128° C.

Sources & evidence

ORD record
ord-b4c625d4dd7648608243494306dcd90c
Source dataset
uspto-grants-2002_03
Patent number
US06362373B1

Reaction notes

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