Acetyl chloride → HCID 12466147, compound

HRID 256344Notes

Reaction equation

HRID 256344 reaction equation
[NH2:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:11]#[N:12].[C:13](Cl)(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([NH:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:11]#[N:12])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 21114833-amino-1-benzofuran-2-carbonitrile

Product 1

HCID 12466147HCID 12466147, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3.86 g (0.024 mole) of 3-amino-2-benzofurancarbonitrile in 50 ml of pyridine is cooled in ice and treated over 15 minutes with 2.0 ml (2.21 g; 0.028 mole) of acetyl chloride. The mixture is stirred in ice an additional two hours and added to 250 g of ice/water. The precipitated crude product is filtered, washed with water, and recrystallized from aqueous methanol to yield 2.8 g (57% yield) of 3-(acetylamino)-2-benzofurancarbonitrile. A sample recrystallized a second time as above is analytically pure, mp 187°-189° C.

Workup

  1. customThe precipitated crude product
  2. filtrationis filtered
  3. washwashed with water
  4. customrecrystallized from aqueous methanol

Sources & evidence

ORD record
ord-2ecdedc9eea7448da960dbf05264f4f4
Source dataset
uspto-grants-1987_10
Patent number
US04703053

Reaction notes

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