Chloroacetaldehyde → 3-Hydroxy-6-(3-nitrophenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazole

HRID 38091

Reaction equation

HRID 38091 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:12]([SH:15])[NH:13][N:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl[CH2:23][CH:24]=[O:25]>C1COCC1.O.CCOC(C)=O.C([O-])(O)=O.[Na+]>[OH:25][CH:24]1[CH2:23][S:15][C:12]2=[C:11]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)=[N:14][N:13]12

Participants

6

Reactant 2

HCID 33ChloroacetaldehydeHCID 178526614HCID 178526614, compound

Product 1

HCID 674426243-Hydroxy-6-(3-nitrophenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazoleYield 72.7%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

5-(3-Nitro-phenyl)-4-pyridin-4-yl-2H-pyrazole-3-thiol (prepared as described in Example 1) (3.92 g, 13.14 mmol) was dissolved in a 1:1 THF/water mixture (130 mL). Chloroacetaldehyde (55% in water, 2.31 mL, 19.71 mmol, 1.5 eq) was added and the solution was stirred at room temperature overnight. The reaction mixture was diluted with AcOEt and saturated aqueous NaHCO3. The organic phase was washed with saturated aqueous NaHCO3 and brine, dried and evaporated to dryness. 3.25 g of crude product were obtained as yellow solid (72%), which was used in the following step without further purification.

Workup

  1. washThe organic phase was washed with saturated aqueous NaHCO3 and brine
  2. customdried
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-077782a335c4497a9139fd5fd4e839e6
Source dataset
uspto-grants-2013_09
Patent number
US08524707B2

Linked notes

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