Chloroacetonitrile → HCID 7193952, compound

HRID 1904883Notes

Reaction equation

HRID 1904883 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([OH:12])=[O:11].[CH2:13]([N:15](CC)CC)[CH3:14].ClCC#N>C(OCC)(=O)C>[C:13]([CH2:14][O:11][C:10]([C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1)=[O:12])#[N:15]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 10331Benzofuran-2-carboxylic acid

Product 1

HCID 7193952HCID 7193952, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

81 g of benzofuran-2-carboxylic acid and 50 g of triethylamine were added to 550 ml of ethyl acetate, and to the mixture were further added 40 g of chloroacetonitrile, and the mixture was refluxed by heating for 3 hours. The deposited crystals were removed and the solvent was distilled off, and the obtained crystals were recrystallized from methanol to thereby obtain 85 g of benzofuran-2-carboxylic acid cyanomethyl ester having a melting point between 74° C. and 76° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 3 hours
  3. customThe deposited crystals were removed
  4. distillationthe solvent was distilled off
  5. customthe obtained crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-b9c9fc1dd72242d5af0fd71a33129116
Source dataset
uspto-grants-1989_06
Patent number
US04840869

Reaction notes

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