Hydrochloric Acid → HCID 46178254, compound

HRID 2380792Notes

Reaction equation

HRID 2380792 reaction equation
[CH3:1][N:2]([N:4]=[N:5][C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([O:13]C)=[O:12])[CH3:3].[OH-].[Na+].Cl>CO.O>[CH3:3][N:2]([N:4]=[N:5][C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([OH:13])=[O:12])[CH3:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 16639509HCID 16639509, compound

Product 1

HCID 46178254HCID 46178254, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-[(dimethylamino)diazenyl]thiophene-2-carboxylate (200 mg, 0.93 mmol) in methanol (10 mL) was added a solution of sodium hydroxide (93 mg, 2.3 mmol) in water (2 mL) and stirred at rt for 2 h. The mixture was diluted with ice cold water and acidified with dil. HCl 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 hexane-ethyl acetate (80:20) as eluents to give the product as an off-white solid (70 mg, 38%), mp 108-110° C. IR (neat) νmax 3402, 3082, 2923, 1708, 1218, 1116, 1066, 1016, 880, 773 cm−1; 1H NMR (400 MHz, CDCl3): δ 12.21 (1H, s), 7.47 (1H, d, J=5.2 Hz), 7.30 (1H, d, J=5.2 Hz), 3.65 (3H, s), 3.28 (3H, s); LC-MS (positive ion mode): m/z 200 (M+H)+.

Workup

  1. additionThe mixture was diluted with ice cold water
  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-32927d07dc9a4b12b90a4504c6ae7db0
Source dataset
uspto-grants-2012_09
Patent number
US08258119B2

Reaction notes

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