Thionyl Chloride → 3-(Chloromethyl)-5-methylaniline

HRID 2277766Notes

Reaction equation

HRID 2277766 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:10])[CH:9]=1)[CH2:5]O.S(Cl)([Cl:13])=O>C(Cl)Cl>[Cl:13][CH2:5][C:4]1[CH:3]=[C:2]([CH:9]=[C:8]([CH3:10])[CH:7]=1)[NH2:1]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15680639(3-Amino-5-methylphenyl)methanol

Product 1

HCID 892397843-(Chloromethyl)-5-methylanilineYield 142.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-amino-5-methyl-benzyl alcohol (6.32 g; 42.8 mmol; GL Syntech LLC, Hatfield, Pa.) in DCM (140 mL) at 0° C. was added dropwise thionylchloride (9.4 mL; 128 mmol). The mixture was allowed to react at room temperature overnight. Then, the mixture was concentrated under reduced pressure. The resulting material was dissolved in DCM again and evaporated to dryness to give crude 3-(chloromethyl)-5-methylaniline (9.5 g).

Workup

  1. customto react at room temperature overnight
  2. concentrationThen, the mixture was concentrated under reduced pressure
  3. dissolutionThe resulting material was dissolved in DCM again
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-9f161d3a50054db99cf032b7f35cbc20
Source dataset
uspto-grants-2015_09
Patent number
US09133171B2

Reaction notes

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