Hydrochloric Acid → HCID 22596842, compound

HRID 1760835Notes

Reaction equation

HRID 1760835 reaction equation
[CH2:1]([N:7]([C:22]1[CH:31]=[CH:30][C:29]2[C:28]([CH3:33])([CH3:32])[CH2:27][CH2:26][C:25]([CH3:35])([CH3:34])[C:24]=2[CH:23]=1)[C:8](=[O:21])[NH:9][C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16]CC)=[O:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[K+].C1COCC1.Cl>C(O)C.O>[CH2:1]([N:7]([C:22]1[CH:31]=[CH:30][C:29]2[C:28]([CH3:33])([CH3:32])[CH2:27][CH2:26][C:25]([CH3:34])([CH3:35])[C:24]=2[CH:23]=1)[C:8](=[O:21])[NH:9][C:10]1[CH:20]=[CH:19][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 22596839HCID 22596839, compound

Product 1

HCID 22596842HCID 22596842, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
45 °C

Procedure

A solution of ethyl 4-[3-hexyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (19) (296 mg, 0.62 mmole) in 8 mL ethanol was treated with 694 mg of potassium hydroxide in 3 mL water. THF (2 mL) was added and the mixture was heated to 45° C. for two hours. The reaction mixture was diluted with 10 mL water and the pH adjusted to 2 with concentrated HCl and then extracted with three 25 mL portions of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to provide a pale yellow solid. The product was purified by trituration in pentane and 231 mg (83%) of 4-[3-hexyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic acid (13) were obtained as a pale yellow solid. M.P.: 176.6-177.1° C.

Workup

  1. extractionextracted with three 25 mL portions of ethyl acetate
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide a pale yellow solid
  6. customThe product was purified by trituration in pentane

Sources & evidence

ORD record
ord-90f38329471141e09ef019957b18984a
Source dataset
uspto-grants-2005_01
Patent number
US06844466B2

Reaction notes

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