Triethylamine → HCID 9068037, compound

HRID 2118988Notes

Reaction equation

HRID 2118988 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(N(CC)CC)C.[CH2:16]([C:18]1[C:22]([C:23](Cl)=[O:24])=[C:21]([CH3:26])[O:20][N:19]=1)[CH3:17]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:23]([C:22]2[C:18]([CH2:16][CH3:17])=[N:19][O:20][C:21]=2[CH3:26])=[O:24])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97423-FluoroanilineHCID 20192365HCID 20192365, compound

Product 1

HCID 9068037HCID 9068037, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 13.3 grams (0.120 mole) of m-fluoroaniline and 20.9 ml. (0.150 mole of triethylamine in 120 ml. of toluene is treated by dropwise addition with 22.5 grams (0.129 mole) of 3-ethyl-5-methyl-4-isoxazole carbonyl chloride in 100 ml. of toluene while maintaining the temperature between 30°-35° during addition. The mixture is stirred at room temperature overnight, filtered and the filtrate washed with 2N hydrochloric acid. The toluene is dried and evaporated with the residue recrystallized from toluene to give N-(m-fluorophenyl)-3-ethyl-5-methyl-4-isoxazole carboxamide (m.p. 99.5°-101° C.).

Workup

  1. additionduring addition
  2. filtrationfiltered
  3. washthe filtrate washed with 2N hydrochloric acid
  4. dry with materialThe toluene is dried
  5. customevaporated with the residue
  6. customrecrystallized from toluene

Sources & evidence

ORD record
ord-74c3d53eedbc44baa89685e3b75ba8f0
Source dataset
uspto-grants-1987_07
Patent number
US04681898

Reaction notes

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