Triethylamine → HCID 13066646, compound

HRID 1606647Notes

Reaction equation

HRID 1606647 reaction equation
[C:1]([O:4][C:5]1[CH:24]=[CH:23][CH:22]=[CH:21][C:6]=1[C:7]([NH:9][C:10]1[CH:19]=[C:18]([NH2:20])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])=[O:8])(=[O:3])[CH3:2].[C:25]([O:28][C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31](Cl)=[O:32])(=[O:27])[CH3:26].C(N(CC)CC)C>O1CCCC1>[C:1]([O:4][C:5]1[CH:24]=[CH:23][CH:22]=[CH:21][C:6]=1[C:7]([NH:9][C:10]1[CH:19]=[C:18]([NH:20][C:31](=[O:32])[C:30]2[CH:34]=[CH:35][CH:36]=[CH:37][C:29]=2[O:28][C:25](=[O:27])[CH3:26])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 796682-Acetoxybenzoyl chlorideHCID 21544117HCID 21544117, compound

Product 1

HCID 13066646HCID 13066646, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 80 ml of tetrahydrofuran were dissolved 2 g of methyl 2-(2'-acetoxybenzamido)-4-aminobenzoate and 11.8 g of 2-acetoxybenzoylchloride, and to the solution was added dropwise a solution of 0.6 g of triethylamine in 5 ml of tetrahydrofuran while stirring under cooling with ice. Ten minutes after completion of the addition, the mixture was returned to room temperature, followed by stirring at that temperature for one hour. The reaction mixture was then poured into diluted hydrochloric acid-ice to precipitate crystals. The crystals were recovered by filtration and recrystallized from methanol to obtain 2.0 g of methyl 2,4-bis(2'-acetoxybenzamido)-benzoate having a melting point between 143° - 145°C. This product was confirmed to be identical to that obtained in Example 6.

Workup

  1. temperatureunder cooling with ice
  2. additionTen minutes after completion of the addition
  3. customwas returned to room temperature
  4. stirringby stirring at that temperature for one hour
  5. customto precipitate crystals
  6. filtrationThe crystals were recovered by filtration
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-7f2dbb821ff94cf0a076934945ae65e9
Source dataset
uspto-grants-1976_04
Patent number
US03953496

Reaction notes

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