o-Chlorophenylacetic acid → Acetyl chloride, 2-(2-chlorophenyl)-

HRID 1049685Notes

Reaction equation

HRID 1049685 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.S(Cl)([Cl:14])=O>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([Cl:14])=[O:11]

Participants

4

Reactant 2

HCID 17124o-Chlorophenylacetic acidHCID 24386Thionyl Chloride

Product 1

HCID 182669Acetyl chloride, 2-(2-chlorophenyl)-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chlorophenylacetic acid (51 mg, 0.3 mmol) was dissolved in ethyl acetate (1.5 mL), the solution was added with thionyl chloride (26 μL, 0.36 mmol), and the mixture was refluxed by heating for 4 hours. The solvent was evaporated under reduced pressure to give 2-chlorophenylacetyl chloride. By using this compound and 5-(4-aminophenyl)-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione (190 mg, 0.6 mmol) obtained in Example 1, (3), the title compound (10 mg, yield 11%) was obtained as pale yellow crystals in the same manner as that of Example 1, (4).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 4 hours
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4b0e1797a5524afa8bab7de8b2d85338
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

Loading…