Acetic Anhydride → HCID 22049779, compound

HRID 1830884Notes

Reaction equation

HRID 1830884 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.[C:23](OC(=O)C)(=[O:25])[CH3:24]>C(O)(=O)C.C(OCC)(=O)C>[CH3:22][C:14]1[CH:15]=[CH:16][C:17]([NH:19][C:23](=[O:25])[CH3:24])=[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

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 22049688HCID 22049688, compound

Product 1

HCID 22049779HCID 22049779, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

4-Methyl-3-[2-(2-methyl-5-nitrophenyl)-1,3-thiazol-4-yl]pyridine (100 mg) and reduced iron (180 mg) were suspended in acetic acid (2 ml)-acetic anhydride (0.04 ml) and the mixture was stirred at 70° C. for 4 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 (43 mg) as colorless powder 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-f7a8c1bb048f4e6fb90d1a69a8893504
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

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