Dimethylformamide → HCID 23024785, compound

HRID 350113Notes

Reaction equation

HRID 350113 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[S:6][CH:7]=1.[OH:14][C:15]1[CH:37]=[CH:36][C:18]([CH2:19][N:20]2[CH:24]=[C:23]([C:25]([O:27]CC)=[O:26])[C:22]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:21]2)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:30]1([C:22]2[C:23]([C:25]([OH:27])=[O:26])=[CH:24][N:20]([CH2:19][C:18]3[CH:17]=[CH:16][C:15]([O:14][CH2:2][C:3]4[N:4]=[C:5]([C:8]5[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=5)[S:6][CH:7]=4)=[CH:37][CH:36]=3)[N:21]=2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2369694-(Chloromethyl)-2-phenyl-1,3-thiazoleHCID 23024811HCID 23024811, compound

Product 1

HCID 23024785HCID 23024785, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-chloromethyl-2-phenylthiazole (1.19 g), ethyl 1-(4-hydroxybenzyl)-3-phenyl-1H-pyrazol-4-carboxylate (1.65 g), potassium carbonate (1.18 g) and N,N-dimethylformamide (25 ml) was stirred overnight at 80° C. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. A mixture of the residue, potassium hydroxide (0.93 g) and ethanol (50 ml) was refluxed for 5 hours. After the reaction solvent was removed under reduced pressure, water was added to the reaction mixture, then the mixture was acidified with 1N hydrochloric acid. The crystals obtained were collected by filtration to yield 3-phenyl-1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-1H-pyrazol-4-carboxylic acid (1.82 g, yield: 76%). This was recrystallized from acetone-hexane. Melting point: 119–120° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. additionA mixture of the residue, potassium hydroxide (0.93 g) and ethanol (50 ml)
  6. temperaturewas refluxed for 5 hours
  7. customAfter the reaction solvent was removed under reduced pressure, water
  8. additionwas added to the reaction mixture
  9. customThe crystals obtained
  10. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-2347fe088cff4d7faa653b8a8594e950
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

Loading…