Sodium Hydroxide → HCID 19370602, compound

HRID 872574Notes

Reaction equation

HRID 872574 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:11]=[C:10]([C:12]([O:14]C)=[O:13])[NH:9][N:8]=2)[N:6]=1.[OH-].[Na+]>C1COCC1.CO>[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[NH:9][N:8]=2)[N:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67170996HCID 67170996, compound

Product 1

HCID 19370602HCID 19370602, compoundYield 123.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-(2-methylthiazol-4-yl)-1H-pyrazole-5-carboxylate (0.586 mmol) in 5 ml of THF and 1 ml of MeOH was treated with 2 ml of 1 M NaOH-solution at RT over three nights. Solvent was evaporated and the residue was taken up in water and washed with DCM. 1 M HCl was added to the water phase until pH was 5. The water phase was washed twice with DCM and neutralized by 1 M sodiumbicarbonate solution. The water phase was evaporated from toluene and the evaporation residual suspended to EtOH. Thus obtained solid was filtered to give 151 mg (123%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 2.69 (s, 3H), 6.68 (s, 1H), 7.60 (s, 1H), 12.89 (bs, 1H).

Workup

  1. customSolvent was evaporated
  2. washwashed with DCM
  3. addition1 M HCl was added to the water phase until pH was 5
  4. washThe water phase was washed twice with DCM
  5. customThe water phase was evaporated from toluene
  6. filtrationThus obtained solid was filtered

Sources & evidence

ORD record
ord-fca62a8bdd7e471a912466facf85ffc3
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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