Hydrochloric Acid → HCID 59237146, compound

HRID 2380794Notes

Reaction equation

HRID 2380794 reaction equation
[CH3:1][N:2]([N:4]=[N:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[S:8][C:7]=1[C:17]([O:19]C)=[O:18])[CH3:3].[OH-].[Na+].Cl>CO.O>[CH3:3][N:2]([N:4]=[N:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[S:8][C:7]=1[C:17]([OH:19])=[O:18])[CH3:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67183833HCID 67183833, compound

Product 1

HCID 59237146HCID 59237146, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-[(dimethylamino)diazenyl]-5-phenylthiophene-2-carboxylate (1.8 g, 6.22 mmol) in methanol (50 mL) was added a solution of sodium hydroxide (1.24 g, 31.1 mmol) in water (15 mL) and stirred at rt for 16 h. The mixture was diluted with ice cold water and acidified with dil. HCl. The mixture was stirred for 30 min and the precipitated solid was filtered, washed with water and dried. The solid was chromatographed over silica gel column using hexane-ethyl acetate (70:30) as eluents to give the product. The crude solid was recrystallized from hexane-chloroform to give the product as a pale pink color solid (1.1 g, 61%), mp 162-166° C. IR (neat)νmax. 2923, 2853, 1708, 1260, 1220, 1173, 1042, 1020, 879, 836 cm−1; 1H NMR (400 MHz, CDCl3): δ 12.15 (1H, br s), 7.58-7.60 (2H, m), 7.44 (1H, s), 7.32-7.40 (3H, m), 3.65 (3H, s), 3.25 (3H, s); 13C NMR (100 MHz, CDCl3): δ 162.8, 153.3, 149.7, 133.3, 129.1, 129.0, 125.9, 120.1, 113.4, 44.3, 37.0; LC-MS (positive ion mode): m/z 298 (M+Na)+.

Workup

  1. additionThe mixture was diluted with ice cold water
  2. stirringThe mixture was stirred for 30 min
  3. filtrationthe precipitated solid was filtered
  4. washwashed with water
  5. customdried
  6. customThe solid was chromatographed over silica gel column
  7. customto give the product
  8. customThe crude solid was recrystallized from hexane-chloroform

Sources & evidence

ORD record
ord-9bcbd50a5bf04181a8f20f057f2401f9
Source dataset
uspto-grants-2012_09
Patent number
US08258119B2

Reaction notes

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