Sodium Hydroxide → HCID 59237152, compound

HRID 2380793Notes

Reaction equation

HRID 2380793 reaction equation
[CH3:1][N:2]([N:4]=[N:5][C:6]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[S:8][C:7]=1[C:14]([O:16]C)=[O:15])[CH3:3].[OH-].[Na+]>CO>[CH3:3][N:2]([N:4]=[N:5][C:6]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[S:8][C:7]=1[C:14]([OH:16])=[O:15])[CH3:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67184092HCID 67184092, compound

Product 1

HCID 59237152HCID 59237152, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-[(dimethylamino)diazenyl]-5-nitrothiophene-2-carboxylate (550 mg) in methanol (10 mL) was added an aqueous solution of sodium hydroxide (0.25 g in 5 mL of water) at rt and stirred the mixture for 14 h. Excess of methanol was evaporated under reduced pressure and the residue was diluted with ice cold water. The solution was acidified with dil. HCl and the solid separated was filtered, washed with water and dried to give the product as a yellow color solid (450 mg, 86%). The crude product was recrystallized from chloroform-methanol (290 mg), mp 184-186° C. 1H NMR (400 MHz, DMSO-d6): δ 13.26 (1H, br s), 8.00 (1H, s), 3.59 (3H, s), 3.25 (3H, s); LC-MS (positive ion mode): m/z 245 (M+H)+.

Workup

  1. customExcess of methanol was evaporated under reduced pressure
  2. additionthe residue was diluted with ice cold water
  3. customthe solid separated
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-9dc93b4be8a24e1787872300c037ccad
Source dataset
uspto-grants-2012_09
Patent number
US08258119B2

Reaction notes

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