Acetic Acid → HCID 13173182, compound

HRID 980358Notes

Reaction equation

HRID 980358 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[N:17]=[C:18]3[N:22]([CH:23]=2)[CH2:21][CH2:20][S:19]3)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C=O.[C:32](O)(=O)C>O1CCOCC1>[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[N:17]=[C:18]3[N:22]([C:23]=2[CH2:32][N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH2:21][CH2:20][S:19]3)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 8083MorpholineHCID 13173170HCID 13173170, compound

Product 1

HCID 13173182HCID 13173182, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1.65 g of 6-(3,5-di-tert-butyl-4-hydroxyphenyl)-2,3-dihydroimidazo[2,1-b]thiazole, 1.8 g of morpholine, 1.7 g of an aqueous 35% formaldehyde solution, 1.5 ml of acetic acid, and 10 ml of dioxane was refluxed for 6 hours. The reaction mixture was concentrated udner reduced pressure and to the residue was added 20 ml of an aqueous 10% potassium carbonate to precipitate crystals, which were recovered by filtration and recrystallized from methanol to provide 0.85 g of 6-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-morpholinomethyl-2,3-dihydroimidazo[2,1-b]thiazole.

Workup

  1. temperaturewas refluxed for 6 hours
  2. concentrationThe reaction mixture was concentrated udner reduced pressure
  3. additionto the residue was added 20 ml of an aqueous 10% potassium carbonate
  4. customto precipitate crystals, which
  5. filtrationwere recovered by filtration
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-8ae33f3e41a74bbeae9e4720b8de3296
Source dataset
uspto-grants-1987_01
Patent number
US04636516

Reaction notes

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