Benzoyl chloride → Benzoylamidoacetonitrile

HRID 1981462Notes

Reaction equation

HRID 1981462 reaction equation
[C:1](Cl)(=[O:8])[C:2]1C=CC=[CH:4][CH:3]=1.NCC#N.BrBr.[C:16]([NH:24][CH2:25][C:26]#[N:27])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O)C#CC>C(OCC)(=O)C.C(N(CC)CC)C>[C:16]([NH:24][CH2:25][C:26]#[N:27])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:16]([NH:24][CH:25]([O:8][CH2:1][C:2]#[C:3][CH3:4])[C:26]#[N:27])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

9

Reactant 5

HCID 7412Benzoyl chlorideHCID 10901AminoacetonitrileHCID 129912-Butyn-1-olHCID 24408Bromine2×HCID 101372Benzoylamidoacetonitrile

Product 2

HCID 101372BenzoylamidoacetonitrileHCID 13630886HCID 13630886, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent3×

Procedure

Benzoylaminoacetonitrile was synthesized in a conventional manner from benzoyl chloride and aminoacetonitrile. Bromine (40 g) was added at a time to a solution of 4.0 g of the benzoylaminoacetonitrile in 200 ml of ethyl acetate at room temperature. When the color of bromine in the reaction solution disappeared, the reaction solution was cooled to 0° to 5° C. 2-Butyn-1-ol (2.1 g) and 5.6 g of triethylamine were dissolved in 10 ml of ethyl acetate, and the solution was added dropwise to the ethyl acetate solution previously cooled. After the addition, the reaction was continued for 30 minutes at room temperature. Triethylamine hydrobromide was separated by filtration, and the filtrate was distilled under reduced pressure to evaporate the solvent. The residue was purified by silica gel column chromatography. By elution with hexane-ethyl acetate, 3.8 g of alpha-benzoylamino-(2-butynyloxy)acetonitrile was obtained as a solid. The yield was 65.5%, and the melting point of the product was 84° to 85.5° C.

Workup

  1. temperaturethe reaction solution was cooled to 0° to 5° C
  2. temperaturepreviously cooled
  3. additionAfter the addition
  4. customTriethylamine hydrobromide was separated by filtration
  5. distillationthe filtrate was distilled under reduced pressure
  6. customto evaporate the solvent
  7. customThe residue was purified by silica gel column chromatography
  8. washBy elution with hexane-ethyl acetate

Sources & evidence

ORD record
ord-a6faebffdbfa4ba391cd77829aa5d57d
Source dataset
uspto-grants-1986_06
Patent number
US04592773

Reaction notes

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