Water → HCID 86660451, compound

HRID 874189Notes

Reaction equation

HRID 874189 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH2:17][N:18]2[N:22]=[N:21][C:20]([C:23]([F:26])([F:25])[F:24])=[N:19]2)[S:11][C:12]=1[C:13]([O:15]C)=[O:14].O.[OH-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH2:17][N:18]2[N:22]=[N:21][C:20]([C:23]([F:26])([F:25])[F:24])=[N:19]2)[S:11][C:12]=1[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67125226HCID 67125226, compound

Product 1

HCID 86660451HCID 86660451, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3.60 g (8.91 mmol) of methyl 4-(2-chlorophenyl)-2-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1,3-thiazole-5-carboxylate were dissolved in 18 ml of dioxane and 6 ml of water and 45% strength aqueous sodium hydroxide solution (10.06 mmol) was added dropwise at 0° C. The reaction was stirred for a further hour and warmed to RT. The ethanol was then removed under reduced pressure, and ice-water (10 ml) was added to the residue. The aqueous phase was extracted with ethyl acetate. The organic phase was discarded. Then the aqueous phase was adjusted to a pH of 3 using hydrochloric acid, and again extracted with ethyl acetate (3×20 ml). The combined organic phases were dried over sodium sulphate. (logP: 2.63; MH+: 390; 1H-NMR (400 MHz, DMSO, ppm): 6.65 (s, 2H), 7.36-7.55 (m, 4H).

Workup

  1. customThe ethanol was then removed under reduced pressure, and ice-water (10 ml)
  2. additionwas added to the residue
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. extractionagain extracted with ethyl acetate (3×20 ml)
  5. dry with materialThe combined organic phases were dried over sodium sulphate

Sources & evidence

ORD record
ord-1798cc04d0374d93a328174edc442143
Source dataset
uspto-grants-2015_03
Patent number
US08980886B2

Reaction notes

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