Acetic Anhydride → HCID 10397459, compound

HRID 2304556Notes

Reaction equation

HRID 2304556 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[NH2:5].C(N(CC)CC)C.[C:18](OC(=O)C)(=[O:20])[CH3:19]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:18](=[O:20])[CH3:19])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 5811103-Fluoro-4-methoxyaniline

Product 1

HCID 10397459HCID 10397459, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-fluoro-4-methoxyaniline (56.4 g; 400 mmol) and triethylamine (56 ml; 400 mmol) in dichloromethane (400 ml) is cooled down using an ice bath. Acetic anhydride (57 ml; 600 mmol) is added dropwise and the reaction mixture is agitated for 3 hours at ambient temperature. The reaction medium is then washed successively with water, with an aqueous solution of 10% sodium bicarbonate then with an aqueous solution saturated in sodium chloride. The organic fraction is dried over sodium sulphate and concentrated under reduced pressure. The residue is recrystallized from an ethyl acetate/pentane mixture in order to produce 66.5 g (91%) of a white solid, m.p. 120° C.

Workup

  1. temperatureis cooled down
  2. washThe reaction medium is then washed successively with water, with an aqueous solution of 10% sodium bicarbonate
  3. dry with materialThe organic fraction is dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is recrystallized from an ethyl acetate/pentane mixture in order

Sources & evidence

ORD record
ord-ccecccd5253b418988bff2b6a11d1c7c
Source dataset
uspto-grants-2002_08
Patent number
US06436951B1

Reaction notes

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