Water → HCID 22282491, compound

HRID 1062671Notes

Reaction equation

HRID 1062671 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:15]([O:17]C)=[O:16])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]#[N:14])[CH:8]=2)[N:6]=1.O.O.[OH-].[Li+]>O1CCCC1>[CH3:1][C:2]1[S:3][C:4]([C:15]([OH:17])=[O:16])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]#[N:14])[CH:8]=2)[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 22282469HCID 22282469, compound

Product 1

HCID 22282491HCID 22282491, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of of 2-methyl-4-(3-cyanophenyl)-5-carbomethoxythiazole from Example 9, Part A (0.96 g, 3.7 mmol) in 20 mL of tetrahydrofuran and 10 mL of water was added lithium hydroxide monohydrate (0.31 g, 7.4 mmol). The resulting mixture was stirred at room temperature for 16 h. The mixture was-concentrated in vacuo, diluted with H2O and saturated aqueous NaHCO3 and extracted with hexane. The organic layer was discarded and the aqueous layer was acidified and extracted twice with ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried over MgSO4 and concentrated in vacuo to afford 0.90 g (99%) of the title compound, which was sufficiently pure to be used without purification. MS(NH3—CI) 245 (M+H)+.

Workup

  1. concentrationThe mixture was-concentrated in vacuo
  2. additiondiluted with H2O and saturated aqueous NaHCO3
  3. extractionextracted with hexane
  4. extractionextracted twice with ethyl acetate
  5. washThe combined ethyl acetate extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-413e4b72583d4d6fa1415527d2b65a19
Source dataset
uspto-grants-2005_11
Patent number
US06962935B2

Reaction notes

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