Sodium Hydroxide → HCID 21463566, compound

HRID 1940608Notes

Reaction equation

HRID 1940608 reaction equation
[F:1][C:2]1[C:7]2[N:8]=[C:9]([CH2:11][CH2:12][C:13]3[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=3)[C:16]([O:18]CC)=[O:17])[S:10][C:6]=2[C:5]([F:24])=[CH:4][C:3]=1[F:25].[OH-].[Na+]>O.O1CCOCC1>[F:1][C:2]1[C:7]2[N:8]=[C:9]([CH2:11][CH2:12][C:13]3[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=3)[C:16]([OH:18])=[O:17])[S:10][C:6]=2[C:5]([F:24])=[CH:4][C:3]=1[F:25]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21463522HCID 21463522, compound

Product 1

HCID 21463566HCID 21463566, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 3-[2-(4,5,7-trifluorobenzothiazol-2-yl)ethyl]benzoate (133 mg, 0.36 mmol) in a mixture of water (5 ml) and dioxane (5 ml) was added dropwise aqueous 2N sodium hydroxide (2 ml) and the mixture was stirred for 7 hours at ambient temperature. The reaction mixture was diluted with water and then washed with ether. The aqueous layer was acidified with 10% hydrochloric acid and extracted with ethyl acetate. After drying, evaporation of the solvent left crude crystals, which were recrystallized from ether to give 3-[2-(4,5,7-trifluorobenzothiazol-2-yl)ethyl]benzoic acid (82 mg, 68%) as colorless crystals.

Workup

  1. washwashed with ether
  2. extractionextracted with ethyl acetate
  3. customAfter drying
  4. customevaporation of the solvent
  5. waitleft crude crystals, which
  6. customwere recrystallized from ether

Sources & evidence

ORD record
ord-09c7f50a1a714b119b4c2c2f9fc85b51
Source dataset
uspto-grants-1997_12
Patent number
US05700819

Reaction notes

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