Water → HCID 59237145, compound

HRID 2380805Notes

Reaction equation

HRID 2380805 reaction equation
[OH-].[NH4+:2].[CH3:3][N:4]([N:6]=[N:7][C:8]1[C:9]([C:13]([O:15]C)=O)=[CH:10][S:11][CH:12]=1)[CH3:5].O>C1COCC1>[CH3:3][N:4]([N:6]=[N:7][C:8]1[C:9]([C:13]([NH2:2])=[O:15])=[CH:10][S:11][CH:12]=1)[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 67183740HCID 67183740, compound

Product 1

HCID 59237145HCID 59237145, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold (0-5° C.) solution of ammonium hydroxide (5 mL) was added a solution of methyl 4-[(dimethylamino)diazenyl]thiophene-3-carboxylate (110 mg) in THF (2 mL) for 5 min and stirred at rt for 36 h. The solution was poured into ice cooled water and extracted with chloroform. The combined chloroform 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 chloroform-methanol (98:2) as eluents to give the product as a pale red color solid (25 mg, 25%), mp 168-172° C. IR (neat) νmax 3324, 3125, 2917, 2851, 1655, 1600, 1367, 1336, 1090 cm−1; 1H NMR (400 MHz, CDCl3): δ 8.55 (1H, br s), 8.19 (1H, d, J=3.6 Hz), 7.15 (1H, d, J=3.6 Hz), 5.84 (1H, br s), 3.56 (3H, br s), 3.19 (3H, br s); LC-MS (positive ion mode): m/z 199 (M+H)+.

Workup

  1. additionThe solution was poured into ice
  2. extractionextracted with chloroform
  3. washThe combined chloroform 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-8a333b08c5f24f25b312900400960658
Source dataset
uspto-grants-2012_09
Patent number
US08258119B2

Reaction notes

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