Ammonium Hydroxide → HCID 69527824, compound

HRID 1829816Notes

Reaction equation

HRID 1829816 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[O:5][CH2:6][C@@H:7]([N:11]1[CH:15]=[C:14]([C:16](OCC)=[O:17])[N:13]=[CH:12]1)[C@@H:8]([OH:10])[CH3:9].[OH-].[NH4+:26]>COCCOC>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[O:5][CH2:6][C@@H:7]([N:11]1[CH:15]=[C:14]([C:16]([NH2:26])=[O:17])[N:13]=[CH:12]1)[C@@H:8]([OH:10])[CH3:9]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 69527339HCID 69527339, compound

Product 1

HCID 69527824HCID 69527824, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of ethyl 1-{(1R,2S)-1-[(3,4-dichlorophenoxy)methyl]-2-hydroxypropyl}-1H-imidazole-4-carboxylate (0.23 g), 28% ammonium hydroxide (12 mL) and 1,2-dimethoxyethane (6 mL) was heated at 100° C. in the stainless steel bottle for 24 hours. After cooling, the reaction mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel (gradient elution; 20:1 to 10:1 chloroform-methanol) to give the product, which was recrystallized from 1:5 n-hexane-ethyl acetate (12 mL) to give 1-{(1R,2S)-1-[(3,4-dichlorophenoxy)methyl]-2-hydroxypropyl}-1H-imidazole-4-carboxamide (81) (0.13 g).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by column chromatography on silica gel (gradient elution; 20:1 to 10:1 chloroform-methanol)
  4. customto give the product, which
  5. customwas recrystallized from 1:5 n-hexane-ethyl acetate (12 mL)

Sources & evidence

ORD record
ord-cce2a23e0ca349849a51bd14a408c1b1
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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