Water → HCID 14479980, compound

HRID 1761672Notes

Reaction equation

HRID 1761672 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[O:7][CH2:8][C:9]1[N:10]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:12][CH:13]=1)([O-])=O.O.C(=O)(O)[O-].[Na+]>C(O)C>[C:14]1([C:11]2[S:12][CH:13]=[C:9]([CH2:8][O:7][C:6]3[CH:5]=[C:4]([NH2:1])[CH:22]=[CH:21][CH:20]=3)[N:10]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 14479978HCID 14479978, compound

Product 1

HCID 14479980HCID 14479980, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 16.0 g (0.05 mol) of 4-[(3-nitrophenoxy)methyl-2-phenylthiazole and 56.5 g (0.25 mol) of stannous chloride dihydrate in 300 ml of absolute ethanol is heated to reflux for 20 hours. The mixture is poured into 2 L of water and made alkaline by the addition of solid sodium bicarbonate. The mixture is extracted twice with 1 L of ethyl acetate. The combined ethyl acetate layers are washed twice with dilute aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain 12.0 g (85%) of an oil, which solidifies. The crystals, m.p. 75°-80° C., MS (CI) 283 (M+H), are used without further purification in subsequent reactions.

Workup

  1. temperatureto reflux for 20 hours
  2. extractionThe mixture is extracted twice with 1 L of ethyl acetate
  3. washThe combined ethyl acetate layers are washed twice with dilute aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-427acf6096e14e4e870fb0760a3694a9
Source dataset
uspto-grants-1989_05
Patent number
US04826990

Reaction notes

Loading…