Sodium Hydroxide → [5-(4-chlorophenyl)-3-methyl-1-(1,3-thiazol-5-yl)-1H-pyrazol-4-yl]acetic acid

HRID 563989Notes

Reaction equation

HRID 563989 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:25])[CH2:6][C:7]1[C:8]([CH3:24])=[N:9][N:10]([C:19]2[S:23][CH:22]=[N:21][CH:20]=2)[C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1>CO>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]2[N:10]([C:19]3[S:23][CH:22]=[N:21][CH:20]=3)[N:9]=[C:8]([CH3:24])[C:7]=2[CH2:6][C:5]([OH:25])=[O:4])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 46899850Methyl[5-(4-chlorophenyl)-3-methyl-1-(1,3-thiazol-5-yl)-1h-pyrazol-4-yl]acetate

Product 1

HCID 46899851[5-(4-chlorophenyl)-3-methyl-1-(1,3-thiazol-5-yl)-1H-pyrazol-4-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 ml of 2 molar aqueous sodium hydroxide solution was added to 0.289 g (0.83 mmol) of methyl[5-(4-chlorophenyl)-3-methyl-1-(1,3-thiazol-5-yl)-1H-pyrazol-4-yl]acetat in 10 ml methanol, and the mixture was stirred at room temperature for four hours and allowed to stand overnight. The mixture was then concentrated, ice-water was added to the residue, and the mixture was adjusted to pH 3-4 by addition of 2 molar aqueous hydrochloric acid and extracted with dichloromethane. The combined organic phases were dried with magnesium sulfate, filtered and dried. The crude product was dried under high vacuum. This gave 0.187 g of product (60.7% of theory); NMR (CDCl3, 400 MHz): 2.33 (s, 3H); 3.39 (s, 2H); 7.24 (d, 2H); 7.31 (br s, 1H); 7.42 (d, 2H); 8.56 (br s, 1H).

Workup

  1. waitto stand overnight
  2. concentrationThe mixture was then concentrated
  3. additionice-water was added to the residue
  4. additionthe mixture was adjusted to pH 3-4 by addition of 2 molar aqueous hydrochloric acid
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined organic phases were dried with magnesium sulfate
  7. filtrationfiltered
  8. customdried
  9. dry with materialThe crude product was dried under high vacuum

Sources & evidence

ORD record
ord-96bc543adfc24ad689088431a45f1ee4
Source dataset
uspto-grants-2011_11
Patent number
US08067611B2

Reaction notes

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