Hydrochloric Acid → (5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)acetic acid

HRID 1416023Notes

Reaction equation

HRID 1416023 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][C:17]([O:19]C)=[O:18])=[N:12][C:11]=2[CH:21]([CH3:23])[CH3:22])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][C:17]([OH:19])=[O:18])=[N:12][C:11]=2[CH:21]([CH3:23])[CH3:22])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54000775methyl [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]acetate

Product 1

HCID 473989(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)acetic acidYield 90.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of methanol (1 ml), 0.10 g of methyl [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]acetate (33)and 1N-sodium hydroxide (0.32 ml)was stirred at room temperature for 1.5 hours. To the reaction mixture was added 0.32 ml of 1N-hydrochloric acid to yield crystals, which were filtered, washed with water and then with chilled methanol to obtain 87 mg of the target compound (Compound I-80)(yield 90%). mp 118° C. (degradation).

Workup

  1. customto yield crystals, which
  2. filtrationwere filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-dd91146e4d3f448f8bfdcd14156b40f7
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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