Ammonia → 4-[4-(1-Adamantyl)-phenoxy]-butyric acid amide

HRID 258974Notes

Reaction equation

HRID 258974 reaction equation
[NH3:1].[C:2]12([C:12]3[CH:24]=[CH:23][C:15]([O:16][CH2:17][CH2:18][CH2:19][C:20](Cl)=[O:21])=[CH:14][CH:13]=3)[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2>C1C=CC=CC=1>[C:2]12([C:12]3[CH:24]=[CH:23][C:15]([O:16][CH2:17][CH2:18][CH2:19][C:20]([NH2:1])=[O:21])=[CH:14][CH:13]=3)[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 540178074-[4-(1-Adamantyl)-phenoxy]-butyric acid chloride

Product 1

HCID 540404584-[4-(1-Adamantyl)-phenoxy]-butyric acid amide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A strong stream of dry ammonia is passed (for 15 minutes) into a solution of 16.5 g of 4-[4-(1-adamantyl)-phenoxy]-butyric acid chloride in 150 ml of absolute benzene under anhydrous conditions, whilst stirring. The product formed is now filtered off and washed with ehter. Recrystallisation from a large amoumt of acetone yields pure 4-[4-(1-adamantyl)-phenoxy]-butyric acid amide of melting point 176°-177° C (needles).

Workup

  1. custom(for 15 minutes)
  2. customThe product formed
  3. filtrationis now filtered off
  4. washwashed with ehter
  5. customRecrystallisation from a large amoumt of acetone

Sources & evidence

ORD record
ord-ee2ee75828f540679cbacda3fd511014
Source dataset
uspto-grants-1977_07
Patent number
US04035413

Reaction notes

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