Hydrochloric Acid → HCID 86760108, compound

HRID 1830883Notes

Reaction equation

HRID 1830883 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([C:13]2[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[CH:15][C:14]=2[CH3:22])[S:11][CH:12]=1.[CH:23](OCC)=[O:24].Cl>C(O)=O.C(OCC)(=O)C>[CH3:22][C:14]1[CH:15]=[CH:16][C:17]([NH:19][CH:23]=[O:24])=[CH:18][C:13]=1[C:10]1[S:11][CH:12]=[C:8]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][C:2]=2[CH3:1])[N:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 22049688HCID 22049688, compound

Product 1

HCID 86760108HCID 86760108, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

4-Methyl-3-[2-(2-methyl-5-nitrophenyl)-1,3-thiazol-4-yl]pyridine (98 mg) and reduced iron (170 mg) were suspended in a mixture of formic acid (3 ml)-ethyl formate (3 ml). 1N Hydrochloric acid (0.2 ml) was added and the mixture was stirred at 80° C. for 12 hrs. The reaction mixture was diluted with ethyl acetate and the insoluble material was filtered off. The organic layer was neutralized with saturated aqueous sodium hydrogen carbonate. The organic layer was separated and concentrated by drying. The residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=1:1–0:1) for purification. Recrystallization from ethyl acetate gave the title compound (15 mg) as pale-yellow columnar crystals.

Workup

  1. filtrationthe insoluble material was filtered off
  2. customThe organic layer was separated
  3. concentrationconcentrated
  4. customby drying
  5. customThe residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=1:1–0:1) for purification
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-88631fde30a74d7d84317c3d437802a8
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

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