Hydrochloric Acid → HCID 49783916, compound

HRID 1097216Notes

Reaction equation

HRID 1097216 reaction equation
[CH3:1][N:2]([N:4]=[N:5][C:6]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[Se:8][C:7]=1[C:15]([O:17]CC)=[O:16])[CH3:3].[OH-].[Na+].Cl>CO.O>[CH3:1][N:2]([N:4]=[N:5][C:6]1[CH:10]=[C:9]([C:11]([CH3:12])([CH3:13])[CH3:14])[Se:8][C:7]=1[C:15]([OH:17])=[O:16])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86646883HCID 86646883, compound

Product 1

HCID 49783916HCID 49783916, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 3-[(dimethylamino)diazenyl]-5-(tert-butyl)selenophene-2-carboxylate (400 mg, 1.2 mmol) prepared as described in Example 4 step c) in methanol (10 mL) was added a solution of sodium hydroxide (240 mg, 6.04 mmol) in water (5 mL) and stirred at room temperature (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 pale brown color solid (160 mg, 45%), mp 120-122° C. IR (neat) νmax 2960, 2927, 1713, 1248, 1180, 1110, 1069, 1010, 844, 767 cm−1; 1H NMR (400 MHz, CDCl3): δ 12.23 (1H, s, —COOH), 7.38 (1H, s, H-4), 3.63 (3H, s, —NCH3), 3.23 (3H, s, —NCH3), 1.39 (9H, s, 3×—CH3); 13C NMR (100 MHz, CDCl3): δ 171.7, 164.1, 153.7, 123.2, 115.6, 44.2, 37.2, 36.9, 32.4; LC-MS (positive ion mode): m/z 324, 326 (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-d79c6afc77304ec5b644b619d9628ad5
Source dataset
uspto-grants-2012_03
Patent number
US08143237B2

Reaction notes

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