Thionyl Chloride → 2-Azidomethylphenylacetyl Chloride

HRID 1111787Notes

Reaction equation

HRID 1111787 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]([OH:14])=O)=[N+:2]=[N-:3].S(Cl)([Cl:17])=O>CN(C)C=O.C(Cl)Cl>[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]([Cl:17])=[O:14])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 3016229(2-(Azidomethyl)phenyl)acetic acid

Product 1

HCID 227677832-Azidomethylphenylacetyl Chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Azidomethylphenylacetic acid (19.1 g., 0.1 mole) was dissolved in 800 ml. of methylene chloride. To this solution was added slowly thionyl chloride (26 g., 0.2 mole) and 0.5 ml. of dimethylformamide as catalyst. The reaction mixture was heated at reflux temperature under nitrogen atmosphere for 1 hour. The methylene chloride solution was concentrated with the aid of vacuum and the residue oil (checked by IR spectroscopy-carboxyl 1800 cm-1 and azido group at 2010 cm-1) was picked up in 100 ml. of acetone and placed into a dropping funnel for use directly in the subsequent acylation reaction.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature under nitrogen atmosphere for 1 hour
  3. concentrationThe methylene chloride solution was concentrated with the aid of vacuum
  4. customof acetone and placed into a dropping funnel for use directly in the subsequent acylation reaction

Sources & evidence

ORD record
ord-d3f0b4bafb0a44399b1e4a96ff576d5c
Source dataset
uspto-grants-1978_10
Patent number
US04118563

Reaction notes

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