Butyl nitrite → Alpha-Oximino-2-Thienylacetonitrile

HRID 461013

Reaction equation

HRID 461013 reaction equation
[Na].[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]#[N:9].C([O:14][N:15]=O)CCC>C(O)C>[N:15](=[C:7]([C:3]1[S:2][CH:6]=[CH:5][CH:4]=1)[C:8]#[N:9])[OH:14]

Participants

5

Reactant 3

HCID 10996Butyl nitriteHCID 728802-ThienylacetonitrileHCID 5360545Sodium

Product 1

HCID 73667355Alpha-Oximino-2-Thienylacetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2.3 g. (0.10 mole) of sodium metal dissolved in 50 ml. ethanol and cooled to 0° C. in an ice bath was added 12.3 g. (0.10 mole) of 2-thienylacetonitrile. After the addition was complete 10.3 g. (0.10 mole) of butylnitrite was added. The reaction was stirred 1 hour at 0° C. and 3 hours at room temperature before the mixture was concentrated to dryness in vacuo. The residue was washed with ether. The sodium salt of the product was dissolved in water and acidified with concentrated hydrochloric acid to a pH of 3. The solid was filtered, washed with water, dried and recrystallized from chloroform to give 6.6 g. of final product which melted at 135°-137° C.

Workup

  1. additionwas added 12.3 g
  2. additionAfter the addition
  3. concentrationwas concentrated to dryness in vacuo
  4. washThe residue was washed with ether
  5. dissolutionThe sodium salt of the product was dissolved in water
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. customdried
  9. customrecrystallized from chloroform
  10. customto give 6.6 g

Sources & evidence

ORD record
ord-e150220b23744cf99eeb3896d5112f4b
Source dataset
uspto-grants-1977_12
Patent number
US04061764

Linked notes

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