Triethylamine → 2-Methyl-6-acetamidobenzyl chloride

HRID 2073798Notes

Reaction equation

HRID 2073798 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11](=[O:13])[CH3:12])[C:3]=1[CH2:4]O.C(N(CC)CC)C.S([Cl:25])(C)(=O)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11](=[O:13])[CH3:12])[C:3]=1[CH2:4][Cl:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 143684642-Methyl-6-acetamidobenzyl alcohol

Product 1

HCID 143684832-Methyl-6-acetamidobenzyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-methyl-6-acetamidobenzyl alcohol (30 g) and triethylamine (46.54 ml) in methylene chloride (300 ml) was added dropwise mesyl chloride (14.25 ml) below 8° C. The mixture was stirred under ice cooling for 30 minutes and then at room temperature for 20 minutes. The reaction mixture was washed with 1N-hydrochloric acid solution, water and saturated sodium bicarbonate aqueous solution, dried over magnesium sulfate and evaporated in vacuo. The residue was suspended in n-hexane and the precipitates were collected by filtration and dried to give 2-methyl-6-acetamidobenzyl chloride (19.28 g).

Workup

  1. waitat room temperature for 20 minutes
  2. washThe reaction mixture was washed with 1N-hydrochloric acid solution, water and saturated sodium bicarbonate aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. filtrationthe precipitates were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-056033a7c31943d38a15c91206144759
Source dataset
uspto-grants-1990_04
Patent number
US04920129

Reaction notes

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