Thionyl Chloride → HCID 86649694, compound

HRID 37836Notes

Reaction equation

HRID 37836 reaction equation
[CH3:1][N:2]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5](O)=[O:6].S(Cl)([Cl:19])=O>ClCCl>[CH3:1][N:2]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]([Cl:19])=[O:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 112530753-[Methyl-(4-nitro-phenyl)-amino]-propionic acid

Product 1

HCID 86649694HCID 86649694, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[Methyl-(4-nitro-phenyl)-amino]-propionic acid (1.2 g, 5.35 mmol) in dichloromethane (10 mL) was cooled to 0° C. and thionyl chloride (1.55 mL, 21.4 mmol) was added. The mixture was heated to reflux for 4 h. The solvent was evaporated to give the crude compound which was azeotroped with toluene to remove the traces of thionyl chloride, affording 3-[methyl-(4-nitro-phenyl)-amino]-propionyl chloride (1.15 g, 88%) as a yellow solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 h
  3. customThe solvent was evaporated
  4. customto give the crude compound which
  5. customwas azeotroped with toluene
  6. customto remove the traces of thionyl chloride

Sources & evidence

ORD record
ord-4c5062c65cb046e6b4d2fa8d50f803c9
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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