Hydrochloric Acid → HCID 9954184, compound

HRID 2108051Notes

Reaction equation

HRID 2108051 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]2[O:13]C(=O)[N:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[CH2:10]2)=[CH:4][C:3]=1[Cl:30].Cl>C1COCC1>[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([CH2:10][NH:11][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[OH:13])=[CH:4][C:3]=1[Cl:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23045061HCID 23045061, compound

Product 1

HCID 9954184HCID 9954184, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(4-amino-3,5-dichlorophenyl)-3-[6-[2-(2-pyridinyl) ethoxy]hexyl]-2-oxazolidinone (80 mg) and 2N hydrochloric acid (1 ml) in THF (5 ml) was heated at 80° for 2 h. The solvent was evaporated and the aqueous residue extracted with ethyl acetate (2×25 ml). The aqueous layer was basified with 2N sodium hydroxide solution to pH10 and extracted with ethyl acetate (3×25 ml). The combined extracts were dried and evaporated to leave a pale yellow gum (70 mg). Crystallisation from ethyl acetate/n-hexane gave the title compound as a white crystalline solid m.p. 97.5°-100°, t.l.c. (System A 39:10:1) Rf 0.44.

Workup

  1. customThe solvent was evaporated
  2. extractionthe aqueous residue extracted with ethyl acetate (2×25 ml)
  3. extractionextracted with ethyl acetate (3×25 ml)
  4. customThe combined extracts were dried
  5. customevaporated

Sources & evidence

ORD record
ord-c62fa2f1fca34698a0962d729b90c9f1
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

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