Ammonium Hydroxide → HCID 69527784, compound

HRID 1829821Notes

Reaction equation

HRID 1829821 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9][CH2:10][C@H:11]([N:15]1[CH:19]=[C:18]([C:20]([O:22]CC)=O)[N:17]=[CH:16]1)[C@@H:12]([OH:14])[CH3:13].[OH-].[NH4+:26]>COCCOC>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9][CH2:10][C@H:11]([N:15]1[CH:19]=[C:18]([C:20]([NH2:26])=[O:22])[N:17]=[CH:16]1)[C@@H:12]([OH:14])[CH3:13]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 69527995HCID 69527995, compound

Product 1

HCID 69527784HCID 69527784, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of ethyl 1-{(1R,2S)-1-{[(2,3-dichlorophenyl)thio]methyl}-2-hydroxypropyl}-1H-imidazole-4-carboxylate (0.17 g), 28% ammonium hydroxide (10 mL) and 1,2-dimethoxyethane (20 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 (elution; 10:1 chloroform-1% ammonium hydroxide/methanol) to give the product, which was recrystallized from 1:1 n-hexane-ethyl acetate (10 mL) to give 1-{(1R,2S)-1-{[(2,3-dichlorophenyl)thio]methyl}-2-hydroxypropyl}-1H-imidazole-4-carboxamide (104) (0.10 g).

Workup

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

Sources & evidence

ORD record
ord-2d4f5d6457a749e9a3ceb83f731b897d
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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