Water → HCID 59237155, compound

HRID 2380784Notes

Reaction equation

HRID 2380784 reaction equation
[OH-].[NH4+:2].[CH3:3][N:4]([N:6]=[N:7][C:8]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[S:10][C:9]=1[C:16]([O:18]C)=O)[CH3:5].O>C1COCC1>[CH3:3][N:4]([N:6]=[N:7][C:8]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[S:10][C:9]=1[C:16]([NH2:2])=[O:18])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 67184092HCID 67184092, compound

Product 1

HCID 59237155HCID 59237155, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold (0-5° C.) solution of ammonium hydroxide (35 mL) was added a solution of methyl 3-[(dimethylamino)diazenyl]-5-nitrothiophene-2-carboxylate (400 mg) in THF (10 mL) for 5 min and stirred at rt for 20 h. The solution was poured into ice cooled water and extracted with ethyl acetate (3×100 mL). The combined organic layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using hexane-ethyl acetate (50:50) as eluents to give the product as a yellow color solid (90 mg, 26%), mp 240-246° C. 1H NMR (400 MHz, DMSO-d6): δ 8.22 (1H, s), 8.05 (1H, s), 7.91 (1H, s), 3.63 (3H, s), 3.26 (3H, s); LC-MS (positive ion mode): m/z 266 (M+Na)+.

Workup

  1. additionThe solution was poured into ice
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationThe solution was filtered
  6. customevaporated the solvent
  7. customThe residue was chromatographed over silica gel column

Sources & evidence

ORD record
ord-366344c268d847cd918ad0954929283f
Source dataset
uspto-grants-2012_09
Patent number
US08258119B2

Reaction notes

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