Triethylamine → Ethyl 3-[[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]benzoate

HRID 840590Notes

Reaction equation

HRID 840590 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14](Cl)=[O:15])=[C:12]([CH3:17])[O:11][N:10]=1.[CH2:18]([O:20][C:21](=[O:29])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([NH2:28])[CH:23]=1)[CH3:19].C(N(CC)CC)C>ClCCl>[CH3:17][C:12]1[O:11][N:10]=[C:9]([C:3]2[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:13]=1[C:14]([NH:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[C:21]([O:20][CH2:18][CH3:19])=[O:29])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 27365813-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chloride

Product 1

HCID 1343410Ethyl 3-[[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2-Chloro-6-fluorophenyl)5-methylisoxaz-4-oyl chloride (7.9 g, 29.0 mmol) was added in portions to a stirred solution of ethyl-3-aminobenzoate (4.0 g, 29.0 mmol) and triethylamine (4.04 mL, 29.0 mmol) in dry dichloromethane at 0° C. Following the final addition, the mixture was allowed to warm to ambient temperature and stir for 1 hour. The solution was washed with 0.5M aqueous hydrochloric acid, brine, aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and evaporated to a foam which was used in subsequent reactions without further purification.

Workup

  1. additionaddition
  2. washThe solution was washed with 0.5M aqueous hydrochloric acid, brine, aqueous sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to a foam which
  6. customwas used in subsequent reactions without further purification

Sources & evidence

ORD record
ord-1ef85004f79e422981d4c1a76fe3734b
Source dataset
uspto-grants-2002_04
Patent number
US06369070B1

Reaction notes

Loading…