Sodium Nitrite → HCID 136331513, compound

HRID 1097224Notes

Reaction equation

HRID 1097224 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[Se:4][C:3]=1[C:11]([NH2:13])=[O:12].[N:14]([O-])=O.[Na+]>S(=O)(=O)(O)O>[C:7]([C:5]1[Se:4][C:3]2[C:11](=[O:12])[NH:13][N:14]=[N:1][C:2]=2[CH:6]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 866468893-Amino-5-tert-butylselenophene-2-carboxamide

Product 1

HCID 136331513HCID 136331513, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice cold solution (0° C.) of 3-amino-5-(tert-butyl)selenophene-2-carboxamide (3.0 g, 12.2 mmol) in concentrated sulfuric acid (50 mL) was added a cold (0° C.) solution of sodium nitrite (0.92 g, 13.4 mmol) in concentrated sulfuric acid (10 mL) for 10 min (while adding, the temperature should keep between −5-0° C.). After addition, the mixture was stirred at 0° C. for 1 h and at rt for 1 h. The reaction mixture was cooled and poured into crushed ice slowly with stirring for 15 min and stirred at the same temperature for 15 min. The solid was filtered, washed with ice cold water and dried to give the product as a off-white color solid (2.4 g, 77%), mp 158-160° C. 1H NMR (400 MHz, CDCl3): δ 7.67 (1H, s, H-7), 1.50 (9H, s, tert-butyl); LC-MS (negative ion mode): m/z 254, 256 (M−H)—.

Workup

  1. additionwhile adding
  2. customshould keep between −5-0° C.
  3. additionAfter addition
  4. temperatureThe reaction mixture was cooled
  5. additionpoured
  6. custominto crushed ice slowly
  7. stirringwith stirring for 15 min
  8. stirringstirred at the same temperature for 15 min
  9. filtrationThe solid was filtered
  10. washwashed with ice cold water
  11. customdried

Sources & evidence

ORD record
ord-1275a230bfbe4816ac5e531fb490dbae
Source dataset
uspto-grants-2012_03
Patent number
US08143237B2

Reaction notes

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