Hydrochloric Acid → HCID 49783915, compound

HRID 1097215Notes

Reaction equation

HRID 1097215 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)[Se:8][C:7]=1[C:17]([O:19]CC)=[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)[Se:8][C:7]=1[C:17]([OH:19])=[O:18])[CH3:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86646881HCID 86646881, compound

Product 1

HCID 49783915HCID 49783915, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 3-[(dimethylamino)diazenyl]-5-phenylselenophene-2-carboxylate (200 mg, 0.56 mmol) prepared as described in Example 3 step c) in methanol (5 mL) was added a solution of sodium hydroxide (113 mg, 2.84 mmol) in water (3 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 product was recrystallized from hexane-chloroform to give the product as a brown color solid (100 mg, 54%), mp 212-214° C. IR (neat) νmax 3566, 2924, 1700, 1253, 1180, 1113, 1070, 1011, 838, 766 cm−; 1H NMR (400 MHz, CDCl3): δ 12.27 (1H, s, —COOH), 7.79 (1H, s, H-4), 7.55-7.57 (2H, m, Ar—H), 7.34-7.39 (3H, m, Ar—H), 3.65 (3H, s, —N—CH3), 3.25 (3H, s, —N—CH3); 13C NMR (100 MHz, CDCl3): δ 163.9, 155.2, 154.6, 135.5, 129.2, 129.1, 126.3, 124.9, 116.6, 44.4, 37.1; LC-MS (positive ion mode): m/z 346, 344 (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 product was recrystallized from hexane-chloroform

Sources & evidence

ORD record
ord-f2988a9edcff46ddb5cb1f8514cb34f5
Source dataset
uspto-grants-2012_03
Patent number
US08143237B2

Reaction notes

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