Benzoyl chloride → Methyl-2-methoxy-5-benzamidobenzoate

HRID 840604Notes

Reaction equation

HRID 840604 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[O:11][CH3:12].C(N(CC)CC)C.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([NH:10][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:7]=[CH:6][C:5]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 89843Methyl 5-amino-o-anisate

Product 1

HCID 22620052Methyl-2-methoxy-5-benzamidobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 9.92 grams (55 mmol) of methyl-2-methoxy-5-aminobenzoate was taken up in 250 ml methylene chloride, treated with 8.4 mL (61 mmol) triethylamine and cooled to 0° C. The reaction mixture was then treated with 8.1 grams (57 mmol) benzoyl chloride in a dropwise fashion. The reaction mixture was stirred for 30 minutes while warming to room temperature. The reaction mixture was diluted with 500 mL of methylene chloride, washed with 200 mL saturated bicarbonate solution and then rewashed with water and brine. The organic phase was dried and evaporated to a flaky white solid (15.7 grams). This material was used without further purification.

Workup

  1. temperaturewhile warming to room temperature
  2. washwashed with 200 mL saturated bicarbonate solution
  3. customThe organic phase was dried
  4. customevaporated to a flaky white solid (15.7 grams)
  5. customThis material was used without further purification

Sources & evidence

ORD record
ord-ac97a016dea644448e4169f99f7faaeb
Source dataset
uspto-grants-2002_04
Patent number
US06369074B1

Reaction notes

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